Skip to main content
SpringerLink
Log in

Recent Advances in the Chemistry of Azulenes and Natural Hydroazulenes

  • Chapter
Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles

Abstract

The beautiful blue pigment, named “azulene” from its color a century ago, is a minor constituent of some essential oils and was also obtained by dehydrogenation of various sesquiterpenoids (azulene precursors, proazulenes or azulenogens). Since 1936, when the fundamental structure of azulene was defined by Pfau and Plattner (186) as the bicyclic ring system (I) with condensed unsaturated five- and seven-membered rings, many chemists have become interested in these compounds because of their unique structure. The structures of most naturally occurring azulenes have since been clarified and many more azulenes have been synthesized.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 16.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Similar content being viewed by others

References

General References

  1. Barton, D. H. R.: Some Recent Advances in the Chemistry of Sesquiterpenoid Lactones. Record Chem. Progr. 18, 125 (1957).

    CAS  Google Scholar 

  2. Barton, D. H. R. and P. de Mayo: Recent Advances in Sesquiterpenoid Chemistry. Quart. Rev. Chem. Soc. (London) 11, 189 (1957).

    CAS  Google Scholar 

  3. Doering, W. V. E.: Tropylium and Related Molecules. In: Theoretical Organic Chemistry, p. 35. London: Butterworths Sci. Publ. 1958.

    Google Scholar 

  4. Gordon, M.: The Azulenes. Chem. Rev. 50, 127 (1952).

    CAS  Google Scholar 

  5. Guenther, E.: The Essential Oils. Vol. IV. New York: Van Nostrand Co. 1950.

    Google Scholar 

  6. Haagen-Smit, A. J.: Azulenes. Fortschr. Chem. organ. Naturstoffe 5, 40 (1948).

    Google Scholar 

  7. —: Sesquiterpenes and Diterpenes. Fortschr. Chem. organ. Naturstoffe 12, I (1955).

    Google Scholar 

  8. Hafner, K.: Neuere Ergebnisse der Azulen-Chemie. Angew. Chem. 70, 419 (1958).

    CAS  Google Scholar 

  9. Heilbrunner, E.: Azulenes. In: D. Ginsburg, Non-Benzenoid Aromatic Compounds, p. 171. New York: Interscience Publ. 1959.

    Google Scholar 

  10. Herout, V.: Über die Prochamazulene. Parfumerie und Kosmetik 40, 12 (1959).

    Google Scholar 

  11. —: Les progrès récents de la chimie des composés sesquiterpéniques. France et ses parfums 3,(14) 15 (1959).

    Google Scholar 

  12. Keller-Schierlein, W. and E. Heilbrunner: Pathways to Azulenes. In: D. Ginsburg, Non-Benzenoid Aromatic Compounds, p. 277. New York: Inter-science Publ. 1959.

    Google Scholar 

  13. Mayo, P. De: The Chemistry of the Perhydroazulene Sesquiterpenoids. Part I. Perfumery Essent. Oil Record 48, 18 (1957).

    Google Scholar 

  14. —: The Chemistry of the Perhydroazulene Sesquiterpenoids. Part II. Perfumery Essent. Oil Record 48, 68 (1957).

    Google Scholar 

  15. —: Mono-and Sesquiterpenoids. New York: Interscience Publ. 1959.

    Google Scholar 

  16. Nozoe, T.: Natural Tropolones and Related Troponoids. Fortschr. Chem. organ. Naturstoffe 13, 234 (1956).

    Google Scholar 

  17. —: Synthesis of Azulenoids from Troponoids. Croat. Chem. Acta 29, 207 (1957).

    CAS  Google Scholar 

  18. —: Tropones and Tropolones. In: D. Ginsburg, Non-Benzenoid Aromatic Compounds, p. 339. New York: Interscience Publ. 1959.

    Google Scholar 

  19. —: Tropylium and Related Compounds. Progr. Organ. Chem. 5, 132 (1961).

    CAS  Google Scholar 

  20. Nozoe, T. and T. Asao: Azulenes and Heptafulvenes. Dai Yuki Kagaku (Comprehensive Organic Chemistry), Asakura Shoten (Tokyo) 13, 439 (1960).

    Google Scholar 

  21. Nozoe, T. and K. Kikuchi: Troponoids with Heterocyclic Ring. Dai Yuki Kagaku (Comprehensive Organic Chemistry), Asakura Shoten (Tokyo) 13, 535 (1960).

    Google Scholar 

  22. Nozoe, T., K. Takase and H. Matsumura: Tropylium Ion and Troponoids. Dai Yuki Kagaku (Comprehensive Organic Chemistry), Asakura Shoten (Tokyo) 13, I (1960).

    Google Scholar 

  23. Pommer, H.: Über den Stand der Forschung auf dem Gebiet der Azulene. Angew. Chem. 62, 281 (1950).

    Google Scholar 

  24. Reid, D. H.: Azulene and Related Substances. Chem. Soc. Symposia, Bristol, 1958. Spec. Publ. No. 12. London: Chem. Soc. 1958.

    Google Scholar 

  25. Simonsen, J. L. and D. H. R. Barton: The Terpenes. Vol. III. Cambridge: Univ. Press. 1952.

    Google Scholar 

  26. Simonsen, J. L. and W. C. J. Ross: The Terpenes. Vol. V. New York: Cambridge Univ. Press. 1957.

    Google Scholar 

  27. Šorm, F., V. Herout and V. Sýkora: Advances in Sesquiterpene Chemistry. Perfumery Essent. Oil Record 50, 679 (1959).

    Google Scholar 

  28. Treibs, W., W. Kirchhof und W. Ziegenbein: Fortschritte der Azulen-chemie seit 1950. Fortschr. chem. Forsch. 3, 334 (1955).

    CAS  Google Scholar 

Special References

  1. Abu-Shady, H. A. and T. O. Soine: The Chemistry of Ambrosia maritima. I. The Isolation and Preliminary Characterization of Ambrosin and Damsin. J. Amer. Pharm. Assoc. 42, 387 (1953).

    CAS  Google Scholar 

  2. 30.— The Chemistry of Ambrosia maritima. II. Hydrogénation, Oxidation, and Dehydrogenation of Ambrosin and Damsin. J. Amer. Pharm. Assoc. 43, 365 (1954).

    CAS  Google Scholar 

  3. Adams, R. and W. Herz: Helenalin. I. Isolation and Properties. J. Amer. Chem. Soc. 71, 2546 (1949).

    CAS  Google Scholar 

  4. —: Helenalin. II. Helenalin Oxide. J. Amer. Chem. Soc. 71, 2551 (1949).

    CAS  Google Scholar 

  5. —: Helenalin. III. Reduction and Dehydrogenation. J. Amer. Chem. Soc. 71, 2554 (1949).

    CAS  Google Scholar 

  6. Akino, H.: Synthesis of Various Azulenes from 4-Methyltropolone. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  7. Alder, K., R. Muders, W. Krane und P. Wirtz: Über die Konstitution photochemisch dargestellter Norcaradien-carbonsäureester. Liebigs Ann. Chem. 627, 59 (1959).

    CAS  Google Scholar 

  8. Amiel, Y. and D. Ginsburg: Alicyclic Studies. XI. Attempted Syntheses of 5:6-Benzazulene and Benzheptalenes. Tetrahedron I, 9 (1957).

    Google Scholar 

  9. Anderson, A. G., Jr., R. G. Anderson and L. L. Replogle: The Reaction of Azulenes with Trifluoroacetic Anhydride. Proc. Chem. Soc. (London) 1960, 72.

    Google Scholar 

  10. Anderson, A. G., Jr. and G. M-C. Chang: Reaction of Azulene with N-Nitrosoacetanilide, Phenylazotriphenylmethane, and Benzoyl Peroxide. J. Organ. Chem. (USA) 23, 151 (1958).

    CAS  Google Scholar 

  11. Anderson, A. G., Jr., C. G. Fritz and R. Scotoni, Jr.: Azulene. VII. A Study of the Beckmann Rearrangement of I,3-Diacetylazulene Dioxime and I,3-Diacetylazulene Dioxime Diacetate. J. Amer. Chem. Soc. 79, 6511 (1957).

    CAS  Google Scholar 

  12. Anderson, A. G., Jr. and R. N. Mcdonald: Azulene. IX. Synthesis of Some Derivatives of I-Azulenethiol and I, 3-Azulenedithiol. J. Amer. Chem. Soc. 8r, 5669 (1959).

    Google Scholar 

  13. Anderson, A. G., Jr. and L. L. Replogle: Electrophilic Substitution of I,3-Dichloroazulene. J. Organ. Chem. (USA) 25, 1275 (1960).

    CAS  Google Scholar 

  14. Anderson, A. G., Jr. and B. M. Steckler: Azulene. VIII. A Study of the Visible Absorption Spectra and Dipole Moments of Some I-and 1,3-Substituted Azulenes. J. Amer. Chem. Soc. 81, 4941 (1959).

    CAS  Google Scholar 

  15. Asano, T.: Syntheses of Azulenic Compounds from Hinokitiol. Thesis, Tohoku Univ., Sendai (Japan), 1959.

    Google Scholar 

  16. Assony, S. J. and N. Kharasch: Derivatives of Sulfenic Acids. XXXII. The Synthesis of Azulenes via the Interactions of Arylacetylenes with Sulfenyl Halides. Part I. 1,2,3-Triphenylazulene. J. Amer. Chem. Soc. 80, 5978 (1958).

    CAS  Google Scholar 

  17. Bach, G., E.-J. Poppe und W. Treibs: Darstellung von stickstoffreien Azulenmonomethin-Farbstoffen. Naturwiss. 45, 517 (1958).

    CAS  Google Scholar 

  18. Balaban, A. T.: Possible Formation of Tetraphenylcyclobutadiene. Tetrahedron Letters 1959, No. 5, 14.

    Google Scholar 

  19. Barton, D. H. R.: Some Aspects of Sesquiterpenoid Chemistry. Proc. Chem. Soc. (London) 1958, 61.

    Google Scholar 

  20. —: Some Jphotochemical Rearrangements. Helv. Chim: Acta 42, 2604 (1959).

    CAS  Google Scholar 

  21. Barton, D. H. R., O. C. Böckman and P. de Mayo: Sesquiterpenoids. Part XII. Further Investigations on the Chemistry of Pyrethrosin. J. Chem. Soc. (London) 1960, 2263.

    Google Scholar 

  22. Barton, D. H. R. and J. E. D. Levisalles: Sesquiterpenoids. Part XI. The Constitution of Geigerin. J. Chem. Soc. (London) 1958, 4518.

    Google Scholar 

  23. Barton, D. H. R. and P. de Mayo: Sesquiterpenoids. Part VII. The Constitution of Tenulin, a Novel Sesquiterpenoid Lactone. J. Chem. Soc. (London) 1956, 142.

    Google Scholar 

  24. — Sesquiterpenoids. Part VIII. The Constitution of Pyrethrosin. J. Chem. Soc. (London) 1957, 150.

    Google Scholar 

  25. Barton, D. H. R., P. De Mayo and M. Shafiq: Photochemical Transformations. Part I. Some Preliminary Investigations. J. Chem. Soc. (London) 1957, 929.

    Google Scholar 

  26. Barton, D. H. R. and C. R. Narayanan: Sesquiterpenoids. Part X. The Constitution of Lactucin. J. Chem. Soc. (London) 1958, 963.

    Google Scholar 

  27. Barton, D. H. R. and J. T. Pinhey: The Stereochemical Correlation of Artemisin and Geigerin. Proc. Chem. Soc. (London) 1960, 279.

    Google Scholar 

  28. Bates, R. B., E. J. Eisenbraun and S. M. Mcelvain: The Configurations of the Nepetalactones and Related Compounds. J. Amer. Chem. Soc. 80, 3420 (1958).

    CAS  Google Scholar 

  29. Bauder, A. und Hs. H. Günthard: Deuterierte Azulene. I. Herstellung und spektroskopische Eigenschaften von Azulen-d2-(I,3). Helv. Chim. Acta 41, 889 (1958).

    CAS  Google Scholar 

  30. Bergmann, E. D. and R. Ikan: 4-and 5-Phenylazulenes. J. Amer. Chem. Soc. 80, 3135 (1958).

    CAS  Google Scholar 

  31. Bernardi, L. and G. BüChi: The Structures of Ambrosin and Damsin. Experientia 13, 466 (1957).

    CAS  Google Scholar 

  32. Bernstein, H. J., J. A. Pople and W. G. Schneider: The Analysis of Nuclear Magnetic Resonance Spectra. I. Systems of Two and Three Nuclei. Canad. J. Chem. 35, 65 (1957).

    CAS  Google Scholar 

  33. Bernstein, H. J., W. G. Schneider and J. A. Pople: The Proton Magnetic Resonance Spectra of Conjugated Aromatic Hydrocarbons. Proc. Roy. Soc. London A 236, 515 (1956).

    CAS  Google Scholar 

  34. Birch, A. J.: The Volatile Oil of Metrosideros scandens. J. Chem. Soc. (London) 1953, 715.

    Google Scholar 

  35. Birch, A. J., D. J. Collins and A. R. Penfold: Zierone: Derivative of a New Natural Azulene. Chem. and Ind. 1955, 1773.

    Google Scholar 

  36. Birch, A. J., J. Grimshaw, R. N. Speake, R. M. Gascoigne and R. O. Hellyer: Aromadendrene and Viridiflorol. Tetrahedron Letters 1959, No. 3, 15.

    Google Scholar 

  37. Birch, A. J. and F. N. Lahey: The Structure of Aromadendrene. I. Austral. J. Chem. 6, 379 (1953).

    CAS  Google Scholar 

  38. Birch, A. J. and K. M. C. Mostyn: A New Sesquiterpene Alcohol from Himantandra baccata BAIL. Austral. J. Chem. 8, 550 (1955).

    CAS  Google Scholar 

  39. Blumann, A., A. R. H. Cole, K. J. L. Thieberg and D, E. White: The Constitution of Globulol. Chem. and Ind. 1954, 1426.

    Google Scholar 

  40. Braun, B. H., W. Herz and K. Rabindran: The Structure of Tenulin. J. Amer. Chem. Soc. 78, 4423 (1956).

    CAS  Google Scholar 

  41. Breslow, R. and M. Battiste: An Unusual Rearrangement in the Cyclo-propene Series. J. Amer. Chem. Soc. 82, 3626 (1960).

    CAS  Google Scholar 

  42. Bruderer, H., D. Arigoni und O. Jeger: Zur Kenntnis der Sesquiterpene und Azulene, 116. Mitt. Über die absolute Konfiguration des α-Santonins. Helv. Chim. Acta 39, 858 (1956).

    CAS  Google Scholar 

  43. Brunken, J. und E.-J. Poppe: Cyaninfarbstoffe aus 2-Methyl-4(azulenyl-I)-thiazol. Chem. Ber. 93, 2572 (1960).

    CAS  Google Scholar 

  44. Büchi, G., S. W. Chow, T. Matsuura, T. L. Popper, H. H. Rennhard and M. S. V. Wittenau: Terpenes. XII. The Constitutions of Aromadendrene, Globulol, Ledol and Viridoflorol. Tetrahedron Letters 1959, No. 6, 14.

    Google Scholar 

  45. Büchi, G. and R. E. Erickson: Terpenes. V. The Structure of Patchouly Alcohol. J. Amer. Chem. Soc. 78, 1262 (1956).

    Google Scholar 

  46. Büchi, G. and D. Rosenthal: Terpenes. VI. The Structures of Helenalin and Isohelenalin. J. Amer. Chem. Soc. 78, 3860 (1956).

    Google Scholar 

  47. Burton, R., L. Pratt and G. Wilkinson: Transition-metal Complexes of Seven-membered Ring Systems. Part II. Azulenemetal Carbonyls. J. Chem. Soc. (London) 1960, 4290.

    Google Scholar 

  48. Burton, R. and G. Wilkinson: An Azulene-Metal Complex. Chem. and Ind. 1958, 1205.

    Google Scholar 

  49. Čekan, Z., V. Herout and F. Šorm: A Chamazulene Precursor from Chamomile (Matricaria chamomilla L.). Chem. and Ind. 1954, 604. —On Terpenes. LXII. Isolation and Properties of the Pro-chamazulene from Matricaria chamomilla L., a Further Compound of the Guaianolide Group. Collect. Czech. Chem. Commun. 19, 798 (1954).

    Google Scholar 

  50. F. Šorm —: Structure of Matricin. Chem. and Ind. 1956, 1234. —Über Terpene. LXXX. Die Struktur von Matricin, ein Guajanolid aus der Kamille (Matricaria chamomilla L.). Collect. Czech. Chem. Commun. 22, 1921 (1957).

    Google Scholar 

  51. Čekan, Z., V. Procházka, V. Herout and F. Šorm: On Terpenes. CI. Isolation and Constitution of Matricarin, another Guaianolide from Camomile (Matricaria chamomilla L.). Collect. Czech. Chem. Commun. 24, 1554 (1959).

    Google Scholar 

  52. V. Herout and F. Šorm —: On Terpenes. CXV. Isolation of Globicin, a Guaianolide from Matricaria globifera (THUNB.) DRUCE. Coll. Czech. Chem. Commun. 25, 2553 (1960).

    Google Scholar 

  53. Chiurdoglu, G., A. Copet and P. Tullen: Study of the Structure of Tri-cyclovetivene of Vetiveria zizanioides Oil. Bull agr. Congo Belge 48, 1503 (1957) [Chem. Abstr. 52, 20906 (1958)].

    Google Scholar 

  54. Chiurdoglu, G. Et J. Decot: Contribution à l’étude des composés sesqui-terpéniques. II. Étude de la structure du bicyclovétivénol et du tricyclovétivénol, alcools primaires de l’essence de vétiver. Tetrahedron 4, 1 (1958).

    CAS  Google Scholar 

  55. Chiurdoglu, G. and M. Descamps: Structure of Carotol. Chem. and Ind. 1959, 1377. —Contribution à l’étude des composés sesquiterpéniques. IV. Étude de la structure du carotol, alcool C15H26O de l’essence de Daucus carota. Tetrahedron 8, 271 (1960).

    CAS  Google Scholar 

  56. Chiurdoglu, G. and P. Tullen: Structure of Tricyclovetivene. Chem. and Ind. 1956, 1094. —Sesquiterpenes. I. Structural Study of Tricyclovetivene from Belgian Congo Vetiver Oil. Bull. soc. chim. Beiges 66, 169 (1957) [Chem. Abstr. 52, 10010 (1958)].

    CAS  Google Scholar 

  57. Clark, E. P.: The Constituents of Certain Species of Helenium. II. Tenulin. J. Amer. Chem. Soc. 61, 1836 (1939).

    CAS  Google Scholar 

  58. —: The Constituents of Certain Species of Helenium. III. The Ester Nature of Tenulin. J. Amer. Chem. Soc. 62, 597 (1940).

    CAS  Google Scholar 

  59. Collins, D. J.: The Structure of Zierone. Part I. The Synthesis of Zierazulene and 6-Methylzierazulene. J. Chem. Soc. (London) 1959, 531.

    Google Scholar 

  60. Corbett, R. E. and R. N. Speden: The Volatile Oil of Pseudowintera colorata. Part II. The Structure of cycloColorenene. J. Chem. Soc. (London) 1958, 3710.

    Google Scholar 

  61. Cowles, E. J.: The Effects of Substituents at the 1-and 3-Positions on the Visible Absorption Spectrum of Azulene. J. Amer. Chem. Soc. 79, 1093 (1957).

    CAS  Google Scholar 

  62. Danyluk, S. S. and W. G. Schneider: Proton Resonance Spectrum and Structure of the Azulinium Ion. J. Amer. Chem. Soc. 82, 997 (1960).

    CAS  Google Scholar 

  63. Djerassi, C., J. Osiecki and W. Herz: Optical Rotatory Dispersion Studies. XIII. Assignment of Absolute Configuration to Certain Members of the Guaianolide Series of Sesquiterpenes. J. Organ. Chem. (USA) 22, 1361 (1957).

    CAS  Google Scholar 

  64. Doering, W. V. E. and D. W. Wiley: Heptafulvene (Methylenecyclohepta-triene). Tetrahedron 11, 183 (1960).

    CAS  Google Scholar 

  65. Dolejš, L., V. Herout, O. Motl, F. Šorm and M. SoučEk: Epimeric Aroma-dendrenes: Stereoisomerism of Ledol, Viridiflorol and Globulol. Chem. and Ind. 1959, 566.

    Google Scholar 

  66. Dolejš, L., V. Herout and F. Šorm: Structure of Palustrol. Chem. and Ind. 1960, 267.

    Google Scholar 

  67. Dolejš, L., A. Mironov and F. Šorm: Structure of Bulnesol. Stereochemistry of Guaiol, Nepetalinic Acids and Iridomyrmecins. Tetrahedron Letters 1960, No. 11, 18.

    Google Scholar 

  68. Dolejš, L., O. Motl, M. Souček, V. Herout and F. Šorm: On Terpenes. CVIII. Epimeric Aromadendrenes. Stereoisomerism of Ledol, Viridiflorol and Globulol. Collect. Czech. Chem. Commun. 25, 1483 (1960).

    Google Scholar 

  69. Dolejš, L. and F. Šorm: Position of the Cyclopropane Ring in Aromadendrene. Tetrahedron Letters 1959, No. 10, 1.

    Google Scholar 

  70. —Stereochemistry of Aromadendrene, Alloaromadendrene, Globulol, Ledol and Viridiflorol. Tetrahedron Letters 1959, No. 17, 1. —On Terpenes. CXIII. Structure of Aromadendrene, alloAromadendrene, Globulol, Ledol and Viridiflorol. Collect. Czech. Chem. Commun. vn25, 1837 (1960).

    Google Scholar 

  71. Dolejš, L., F. Šorm and M. SoučEk: Structure of Ledol and its Stereoisomerism with Globulol. Chem. and Ind. 1959, 160.

    Google Scholar 

  72. Dolejš, L., M. Souček, M. Horák, V. Herout and F. Šorm: Structure of Lactucin. Chem. and Ind. 1958, 530.

    Google Scholar 

  73. Dolejš, L., M. Souček, M. Horák and F. Šorm: The Structure of Ledol. Chem. and Ind. 1958, 494. — On Terpenes. XCVII. The Constitution of Ledol. Collect. Czech. Chem. Commun. 24, 1353 (1959).

    Google Scholar 

  74. Eisenbraun, E. J., T. George, B. Riniker and C. Djerassi: Terpenoids. XLIII. On the Absolute Configuration on Guaiol. Correlation with Nepetalinic Acid. J. Amer. Chem. Soc. 82, 3648 (1960).

    CAS  Google Scholar 

  75. Eschenmoser, A., L. Ruzicka, O. Jeger und D. Arigoni: Zur Kenntnis der Triterpenene, 190. Mitt. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen. Helv. Chim. Acta 38, 1890 (1955).

    CAS  Google Scholar 

  76. Gerdil, R. und E. Heilbronner: Zur Kenntnis der Sesquiterpene und Azulene, 122. Mitt. Azulenaldehyde und Azulenketone: Die polarographische Reduktion von sterisch gehinderten Azulenketonen. Helv. Chim. Acta 40, 141 (1957).

    CAS  Google Scholar 

  77. Gerson, F., T. GäUmann und E. Heilbronner: Elektronenstruktur und physikalisch-chemische Eigenschaften von Azo-Verbindungen. Teil III: Dipolmomente substituierter Phenyl-azo-azulene. Helv. Chim. Acta 41, 1481 (1958).

    CAS  Google Scholar 

  78. Gerson, F. und E. Heilbronner: Elektronenstruktur und physikalischchemische Eigenschaften von Azo-Verbindungen. Teill: Aryl-azo-azulene und Aryl-azo-guaj-azulene. Helv. Chim. Acta 41, 1444 (1958).

    CAS  Google Scholar 

  79. Gerson, F. und E. Heilbronner: Elektronenstruktur und physikalischchemische Eigenschaften von Azo-Verbindungen. Teil IV: LCAO-MO-Modelle des Phenyl-azo-azulens. HelvI-Chim. Acta 41, 2332 (1958).

    CAS  Google Scholar 

  80. — Elektronenstruktur und Physikalisch-Chemische Eigenschaften Von Azo-Verbindungen. Teil V: Über den Einfluß von Substituenten auf das Absorptions-Spektrum des Phenyl-azo-azulens, ein Beitrag zur Kenntnis der Plattner’schen Verschièbungsregel. Helv. Chim. Acta 42, 1877 (1959).

    CAS  Google Scholar 

  81. Gerson, F., J. Schulze und E. Heilbrunner: Elektronenstruktur und physikalisch-chemische Eigenschaften von Azo-Verbindungen. Teil II: Substituierte Phenyl-azo-azulene. Helv. Chim. Acta 41, 1463 (1958).

    CAS  Google Scholar 

  82. E. Heilbrunner —: Elektronenstruktur und Physikalisch-Chemische Eigenschaften Von Azo-Verbindungen. Teil Vii: Notiz über das Absorptions-Spektrum und die Basizität des p-Trimethylammonium-phenyl-azo-azulen-Kations. Helv. Chim. Acta 43, 517 (1960).

    CAS  Google Scholar 

  83. Govindachari, T. R., B. R. Pai, K. K. Purushothaman and S. Rajadurai: Structure of Jatamansone. Chem. and Ind. 1960, 1059.

    Google Scholar 

  84. Govindachari, T. R., K. K. Purushothaman und S. Rajadurai: Struktur von Jatamanson. II. Synthese einiger Trialkylazulene. Chem. Ber. 92, 1662 (1959).

    CAS  Google Scholar 

  85. Govindachari, T. R., S. Rajadurai und B. R. Pai: Struktur von Jatamanson. I. Chem. Ber. 91, 908 (1958).

    CAS  Google Scholar 

  86. Haagen-Smit, A. J. and C. T. O. Fong: Chemical Investigation in Guayule. II. The Structure of Partheniol, a Sesquiterpene Alcohol from Guayule. J. Amer. Chem. Soc. 70, 2075 (1948).

    CAS  Google Scholar 

  87. Hafner, K.: Neuere Untersuchungen über Azulene. Angew. Chem. 70, 413 (1958).

    Google Scholar 

  88. —: Neue quasi-aromatische Verbindungen. Angew. Chem. 71, 378 (1959).

    Google Scholar 

  89. —: Neue Reaktionen des Cyclopentadiens. Angew. Chem. 72, 574 (1960).

    Google Scholar 

  90. Hafner, K. und C. Bernhard: Zur Kenntnis der Azulene, IV. Azulen-Aldehyde und-Ketone. Liebigs Ann. Chem. 625, 108 (1959).

    CAS  Google Scholar 

  91. Hafner, K. und H. Kaiser: Zur Kenntnis der Azulene, III. Eine einfache Synthese substituierter Azulene. Liebigs Ann. Chem. 618, 140 (1958).

    CAS  Google Scholar 

  92. Hafner, K. und H. Pelster: Synthese und Reaktionen von Azulenium-salzen. Angew. Chem. 72, 781 (1960).

    Google Scholar 

  93. Hafner, K. und J. Schneider: Synthese eines Heptalens. Angew. Chem. 70. 702 (1958).

    CAS  Google Scholar 

  94. — Darstellung und Eigenschaften von Derivaten des Pentalens und Heptalens. Liebigs Ann. Chem. 624, 37 (1959).

    CAS  Google Scholar 

  95. Hafner, K. und K.-H. Vöpel: Fulven-Aldehyde. Angew. Chem. 71, 672 (1959).

    CAS  Google Scholar 

  96. Hamilton, J. A., A. T. Mcphail and G. A. Sim: The Structure of Acetyl-bromogeigerin. Proc. Chem. Soc. (London) 1960, 278.

    Google Scholar 

  97. Hendrickson, J. B.: Stereochemical Implications in Sesquiterpene Biogenesis. Tetrahedron 7, 82 (1959).

    CAS  Google Scholar 

  98. Herout, V., L. Dolejš and F. Šorm: The Structure of Artabsin, the Prochain-azulenogen from Artemisia absinthium L. Chem. and Ind. 1956, 1236. — On Terpenenes. LXXIX. On the Structure of Artabsin, a Prochamazulenogen from Wormwood (Artemisia absinthium L.). Collect. Czech. Chem. Commun. 22, 1914 (1957).

    Google Scholar 

  99. Herout, V., M. Holub, L. Novotný, F. Šorm and V. SýKora: Constitution of Carotol and Daucol. Chem. and Ind. 1960, 662.

    Google Scholar 

  100. Herout, V., M. HoráK, B. Schneider and F. Šorm: Location of the Double Bonds in Germacrone. Some Properties of its Spectra. Chem. and Ind. 1959, 1089.

    Google Scholar 

  101. Herout, V., L. Novotný und F. Šorm: Über Pflanzenstoffe. V. Die Isolierung von weiteren kristallinen Substanzen aus Wermut (Artemisia absinthium L.). Collect. Czech. Chem. Commun. 21, 1485 (1956).

    CAS  Google Scholar 

  102. Herout, V. and F. Šorm: On the Composition of Wormwood (Artemisia absinthium L.) and the Isolation of a Crystalline Pro-chamazulenogen. Collect. Czech. Chem. Commun. 18, 854 (1953).

    CAS  Google Scholar 

  103. —: On Terpenes. LXI. Contribution to the Constitution of Pro-chamazulenogen, the Natural Precursor of Chamazulene in Artemisia absinthium L. Collect. Czech. Chem. Commun. 19, 792 (1954); Chem. Listy 48, 706 (1954).

    CAS  Google Scholar 

  104. Über Terpene. LXX. Monocyclische Lactone aus Wermut (Artemisia absinthium L.). Collect. Czech. Chem. Commun. 21, 1494 (1956).

    Google Scholar 

  105. Herz, W.: Azulenes. VIII. I-and 2-t-Butylazulene. Migration of the t-Butyl Group. J. Amer. Chem. Soc. 80, 1243 (1958).

    CAS  Google Scholar 

  106. —: Azulenes. IX. Migration of the Isopropyl Group during the Synthesis of I-Isopropyl-8-methylazulene. J. Amer. Chem. Soc. 80, 3139 (1958).

    CAS  Google Scholar 

  107. Herz, W., P. Jayaraman and H. Watanabe: Constituents of Helenium Species. IX. The Sesquiterpene Lactones of H. flexuosum RAF. and H. campestre SMALL. J. Amer. Chem. Soc. 82, 2276 (1960).

    CAS  Google Scholar 

  108. Herz, W. and R. B. Mitra: Constituents of Helenium Species. VI. Correlation of Helenalin and Alloisotenulin. J. Amer. Chem. Soc. 80, 4876 (1958).

    CAS  Google Scholar 

  109. Herz, W., R. B. Mitra and P. Jayaraman: Constituents of Helenium Species. VIII. Isolation and Structure of Balduilin. J. Amer. Chem. Soc. 81, 6601 (1959).

    Google Scholar 

  110. Herz, W., R. B. Mitra, K. Rabindran and W. A. Rohde: Constituents of Helenium Species. VIL Bitter Principles of H. pinnatifidum (NUTT.) RYDB., H. vernale WALT., H. brevifolium (NUTT.) A. WOOD and H. flexuosum RAF. J. Amer. Chem. Soc. 81, 1481 (1959).

    CAS  Google Scholar 

  111. Herz, W. and H. Watanabe: Parthenin, a New Guaianolide. J. Amer. Chem. Soc. 81, 6088 (1959).

    CAS  Google Scholar 

  112. Hildebrand, R. P. and M. D. Sutherland: Terpenoid Chemistry. I. Zierone and Elleryone. Austral. J. Chem. 12, 436 (1959) [Chem. Abstr. 53, 22061 (1959)].

    CAS  Google Scholar 

  113. House, W. T. and M. Orchin: A Study of the Selenium Dehydrogenation of Guaiol and Related Compounds. Selenium as a Hydrogen Transfer Agent. J. Amer. Chem. Soc. 82, 639 (1960).

    CAS  Google Scholar 

  114. Hunt, G. R. and I. G. Ross: Spectrum of Azulene. Part I. Infrared Spectrum. J. Mol. Spectr. 3, 604 (1959).

    CAS  Google Scholar 

  115. Jefferies, P. R., G. J. H. Melrose and D. E. White: Structure of Aroma-dendrene, Globulol and Ledol. Chem. and Ind. 1959, 878.

    Google Scholar 

  116. Jones, T. G. H. and S. E. Wright: Essential Oils from the Queensland Flora. XXI. The Essential Oil of Evodia elleryana. Univ. Queensland Papers, Dept. Chem. I,(27) 7 (1946) [Chem. Abstr. 41, 1391 (1947)].

    Google Scholar 

  117. Jost, K. H.: Röntgenstrukturanalyse des Chamazulens. Naturwiss. 43, 224 (1956).

    CAS  Google Scholar 

  118. Julg, A.: Étude de l’azulène par la méthode du champ moléculaire selt-consistant. J. chim. phys. 52, 377 (1955).

    CAS  Google Scholar 

  119. Jutz, C.: Synthese von Azulen-polyenalen. Angew. Chem. 70, 270 (1958).

    CAS  Google Scholar 

  120. —: Zwei neue Synthesen von Polyenalen und ungesättigten Ketonen durch Reaktion vinyloger Acylamide. (Darstellung des ds-Nonadien-(2,6)als, Veilchen-blätteraldehyds.) Angew. Chem. 71, 380 (1959).

    Google Scholar 

  121. Kirby, E. C. and D. H. Reid: Conjugated Cyclic Hydrocarbons and Their Heterocyclic Analogues. Part II. The Condensation of Azulenes with Homocyclic and Heterocyclic Aromatic Aldehydes in the Presence of Perchloric Acid. J. Chem. Soc. (London) 1960, 494.

    Google Scholar 

  122. — 4, 6, 8-Trimethylazulenium Perchlorate. Chem. and Ind. 1960, 1217.

    Google Scholar 

  123. Kiryalov, N. P.: Structure of Ledol. Sbornik Statei Obshchei Khim. 2, 1617 (1953) [Chem. Abstr. 49, 5389 (1955)].

    CAS  Google Scholar 

  124. —: Structure of Palustrol. Zhurn. Obshchei Khimii 24, 1271 (1954) [Chem. Abstr. 49, 13944 (1955)].

    CAS  Google Scholar 

  125. Kitahara, Y. and K. Doi: Studies on Heptafulvenes. II. Condensation Reaction of Tropone and Some Active Methylene Compounds. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  126. Kitahara, Y., K. Doi and Y. Sato: Studies on Heptafulvenes. III. (to be published).

    Google Scholar 

  127. Kondo, H. und K. Takeda: Über die Bestandteile der Wurzel von Lindera strychnifolia VILL. (III. Mitt.). J. pharmac. Soc. Japan 59, 504 (1939).

    CAS  Google Scholar 

  128. KřEpinský, J., M. Romaňuk, V. Herout and F. Šorm: Constitution of Valeranone. Tetrahedron Letters 1960, No. 7, 9.

    Google Scholar 

  129. Kurita, Y. and M. Kubo: The Dipole Moments and Electronic Structures of Some Azulene Derivatives. J. Amer. Chem. Soc. 79, 5460 (1957).

    CAS  Google Scholar 

  130. Matsui, K.: Synthesis of 3-Methoxythieno[3,2-a]azulenes. J. Chem. Soc. Japan 82 (1961) (in press).

    Google Scholar 

  131. —Synthesis of Thieno[3, 2-a] azulenes. J. Chem. Soc. Japan 82 (in press) (1961).

    Google Scholar 

  132. —Synthesis of 5-and 7-Isopropylthieno[3,2-a]azulenes. J. Chem. Soc. Japan 82 (1961) (in press).

    Google Scholar 

  133. —Synthesis of 6-Isopropylthieno[3, 2-a]azulenes. J. Chem. Soc. Japan 82 (1961) (in press).

    Google Scholar 

  134. —Cationoid Substitution of Thieno[3,2-a]azulenes. J. Chem. Soc. Japan 82 (1961) (in press).

    Google Scholar 

  135. Matsui, K, and T. Nozoe: Synthesis of Thieno[3,2-a]azulene. Chem. and Ind. 1960, 1302.

    Google Scholar 

  136. Matsumura, S.: Reaction of Troponoid with Ethyl Cyanoacetate and Diethyl α-Cyano-β-iminoglutarate. Thesis, Tohoku Univ., Sendai (Japan), 1960.

    Google Scholar 

  137. Mazur, Y. and A. Meisels: The Structure of Arborescine, a New Sesquiterpene from Artemisia arborescens L. Chem. and Ind. 1956, 492.

    Google Scholar 

  138. Miyazaki, M.: Studies on Azulenes. X. 3-Aminomethyl-S-guaiazulenes. Pharm. Bull. Japan 8, 146 (1960).

    CAS  Google Scholar 

  139. Miyazaki, M., M. Hashi and T. Ukita: Studies on Azulenes. IX. 3-(I-Hydroxy-ethyl)-S-guaiazulene. Chem. Pharm. Bull. Japan 8, 146 (1960).

    CAS  Google Scholar 

  140. Miyazaki, M., H. Watanabe, M. Hashi and T. Ukita: Studies on Azulenes. V. S-Guaiazulene-3-sulfonic Acid. Pharm. Bull. Japan 5, 417 (157).

    Google Scholar 

  141. MÖrikofer, A. und E. Heilbronner: Elektronenstruktur und physikalischchemische Eigenschaften von Azo-Verbindungen. Teil VI: Die relative Basizität von Aryl-azo-azulenen in den Systemen Äthanol/Salzsäure und Methyliso butylketon/Schwefelsäure. Helv. Chim. Acta 42, 1909 (1959).

    Google Scholar 

  142. Motl, O., V. Herout and F. Šorm: On Terpenes. CXII. The Composition of the Oil from Juniperus oxycedrus L. Berries. Collect. Czech. Chem. Commun. 25, 1656 (1960).

    CAS  Google Scholar 

  143. Naito, S.: Studies on the Components of Carpesium abrotanoides. IV. Chemical Structure of Carpesia Lactone (3). J. pharmac. Soc. Japan 75, 39 (1955).

    Google Scholar 

  144. —: Studies on the Components of Carpesium abrotanoides. V. Chemical Constitution of Carpesia Lactone (4). J. pharmac. Soc. Japan 75, 325 (1955).

    CAS  Google Scholar 

  145. Novotný, L., V. Herout and F. Šorm: A Contribution to the Structure of Absinthin and Anabsinthin. Chem. and Ind. 1958, 465. — On Terpenes. CIX. A Contribution to the Structure of Absinthin and Anabsinthin. Collect. Czech. Chem. Commun. 25, 1492 (1960).

    Google Scholar 

  146. On Terpenes. CX. A Contribution to Stereochemistry of Absinthin and Artabsin. Collect. Czech. Chem. Commun. 25, 1500 (1960).

    Google Scholar 

  147. Nozoe, T., Y. Kitahara, K. Takase, I. Murata and R. Hayashi: The Reaction of 3-Carboxytropolone and 3-Cyanotropolone with Hydrazine. Bull. Chem. Soc. Japan 34 (1961) (in press).

    Google Scholar 

  148. Nozoe, T., S. Matsumura, Y. Murase and S. Seto: Synthesis of 2-Amino-azulene Derivatives from 2-Halogenotropones. Chem. and Ind. 1955, 1257.

    Google Scholar 

  149. Nozoe, T., T. Mukai and K. Osaka: Synthesis and Reactions of 8,8-Di-substituted Heptafulvenes. Bull. Chem. Soc. Japan 34 (1961) (in press).

    Google Scholar 

  150. Nozoe, T. and A. Sato: Synthesis of Amino Acids with Azulene Nucleus. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  151. Nozoe, T., S. Seto and T. Asano: Synthesis of Azulene Derivatives from Hinokitiol Methyl Ether. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  152. —6-Isopropylazulene and its Derivatives. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  153. Nozoe, T., S. Seto and S. Matsumura: Synthesis of Azulene Derivatives from Troponoids and Ethyl Cyanoacetate. Bull. Chem. Soc. Japan 34 (1961) (in press).

    Google Scholar 

  154. —Synthesis of Furo[3,2-f]azulene Derivatives. Bull. Chem. Soc. Japan 34 (1961) (in press).

    Google Scholar 

  155. Nozoe, T., S. Seto, S. Matsumura and T. Asano: Synthesis of Azulene Derivative from Troponoids and Cyanoacetic Ester. Proc. Japan Acad. 32, 339 (1956).

    CAS  Google Scholar 

  156. Nozoe, T., S. Seto, S. Matsumura and T. Kusunose: Synthesis of Azulenes with Cyano-and Carboxyl Group at 5-and 6-Positions. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  157. Nozoe, T., S. Seto, S. Matsumura and A. Sato: Synthesis of 2-Substituted Azulene Derivatives. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  158. Nozoe, T., S. Seto and S. Nozoe: Synthesis of Azulene and I-Azaazulanone Derivatives by the Application of Cyanoacetamide to Tropolone and 4-Methyl-tropolone Methyl Ethers. Proc. Japan Acad. 32, 472 (1956).

    CAS  Google Scholar 

  159. Nozoe, T., S. Seto and T. Sato: Synthesis of Azulene Derivatives from 5-Chlorotropolone. Bull. Chem. Soc. Japan 34 (1961) (in press).

    Google Scholar 

  160. Nozoe, T., K. Takase and T. Kusunose: On 4-(5-Pyrazolyl)tropolones. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  161. On 4-(2-Quinolyl)tropolones. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  162. Nozoe, T., K. Takase and M. Tada: Synthesis of 5-and 6-Acetylazulene Derivatives. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  163. —Synthesis of 5-and 6-Aminoazulene Derivatives. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  164. Pyrazolo[4,5-f]azulene Derivatives. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  165. Nozoe, T., K. Takase and K. Umino: Synthesis of s-Ethylazulene Derivatives. Bull. Chem. Soc. Japan (to be published).

    Google Scholar 

  166. Nozoe, T. and Co-Workers: unpublished data.

    Google Scholar 

  167. Ohloff, G., H. Farnow, W. Philipp und G. Schade: Über Germacron und seine pyrolytische Umwandlung. Liebigs Ann. Chem. 625, 206 (1959).

    CAS  Google Scholar 

  168. Palmade, M. Et G. Ourisson: La structure de l’α-gurjunène (Note préliminaire). Bull. soc. chim. France 1958, 886.

    Google Scholar 

  169. Pariser, R.: Electronic Spectrum and Structure of Azulene. J. Chem. Physics 25, 1112 (1956).

    CAS  Google Scholar 

  170. Pauson, P. L.: Hydrocarbon Metal Carbonyls. (Tilden Lecture.) Proc. Chem. Soc. (London) 1960, 297.

    Google Scholar 

  171. Perold, G. W.: The Structure of Geigerin. J. Chem. Soc. (London) 1957, 47.

    Google Scholar 

  172. Pfau, A. St. und Pl. A. Plattner: Zur Kenntnis der flüchtigen Pflanzenstoffe. IV. Über die Konstitution der Azulene. Helv. Chim. Acta 19, 858 (1936).

    Google Scholar 

  173. —: Études sur les matières végétales volatiles. XL Sur la constitution de la β-vétivone. Helv. Chim. Acta 23, 768 (1940).

    CAS  Google Scholar 

  174. Plattner, Pl. A. und E. Heilbronner: Über die Konstitution des Lactaro-violins. Experientia I, 233 (1945).

    Google Scholar 

  175. Plattner, Pl. A., E. Heilbronner, R. W. Schmid, R. Sandrin and A. FüRst: The Structure of Lactaroviolin. Chem. and Ind. 1954, 1202.

    Google Scholar 

  176. Plattner, Pl. A. und L. Lemay: Zur Kenntnis der Sesquiterpene. Über das Kohlenstoff-Gerüst des Guajols und des Guaj-azulens. Helv. Chim. Acta 23, 897 (1940).

    CAS  Google Scholar 

  177. Pommer, H. und K.-D. Möhle: Über das 4-, 5-und 6-Phenyl-azulen. Arch. Pharmaz. 291, 23 (1958).

    Google Scholar 

  178. Poppe, E.-J. und W. Treibs: Darstellung von Azulenstyryl-Farbstoffen. Naturwiss. 45, 517 (1958).

    CAS  Google Scholar 

  179. Rao, A. S., K. B. Butt, S. Dev and P. C. Guha: Sesquiterpenes. XL Sesquiterpenes of the Essential Oil of Lansium annamalayanum. Structure of αChigadmarene. J. Indian Chem. Soc. 29, 620 (1952) [Chem. Abstr. 47, 8698 (1953)].

    CAS  Google Scholar 

  180. Rao, A. S. and M. S. Muthana: Synthesis of i-Ethyl-and 5-Ethylazulenes. J. Indian Inst. Sci. 37 A, 79 (1955) [Chem. Abstr. 50, 3377 (1956).

    CAS  Google Scholar 

  181. Reid, D. H., W. H. Stafford and W. L. Stafford: The Azulene Series. Part IV. The Synthesis and Properties of 3-Acetylguaiazulenes. J. Chem. Soc. (London) 1958, 1118.

    Google Scholar 

  182. Reid, D. H., W. H. Stafford, W. L. Stafford, G. Mclennan and A. Voigt: The Azulene Series. Part III. The Synthesis and Properties of 3-Benzylidene-guaiazulenium Chloride. J. Chem. Soc. (London) 1958, 1110.

    Google Scholar 

  183. Reid, D. H., W. H. Stafford and J. P. Ward: The Azulene Series. Part II. The Synthesis and Properties of Alkoxyazulenes. J. Chem. Soc. (London) 1958, 1100.

    Google Scholar 

  184. Robertson, J. M., H. M. M. Shearer, G. A. Sim and D. G. Watson: A Revision of the Azulene Structure. Nature (London) 182, 177 (1958).

    CAS  Google Scholar 

  185. Romaňuk, M. and V. Herout: On Terpenes. CXIV. On Stereoisomeric Vetivanes and Sesquiterpenic Hydrocarbons of Vétiver Oil. Coll. Czech. Chem. Commun. 25, 2540 (1960).

    Google Scholar 

  186. Romaňuk, M., V. Herout and F. Šorm: On Terpenes. LXIX. The Constitution of Dehydrocostuslactone. Collect. Czech. Chem. Commun. 21, 894 (1956).

    Google Scholar 

  187. Ruzicka, L.: The Isoprene Rule and the Biogenesis of Terpenic Compounds. Experientia 9, 357 (1953).

    CAS  Google Scholar 

  188. —: Bedeutung Der Theoretischen Organischen Chemie FüR Die Chemie Der Terpenverbindungen. In: A. Todd, Perspectives in Organic Chemistry, p. 265. New York: Interscience Publ. 1959.

    Google Scholar 

  189. Schneider, W. G., H. J. Bernstein and J. A. Pople: The Proton Magnetic Resonance Spectra of Azulene and Acepleiadylene. J. Amer. Chem. Soc. 80, 3497 (1958).

    CAS  Google Scholar 

  190. Schulze, J. und E. Heilbrunner: Zur Kenntnis der Sesquiterpene und Azulene, 124. Mitt. Basizität und Absorptions-Spektren des I-Aminoazulens. Helv. China. Acta 41, 1492 (1958).

    CAS  Google Scholar 

  191. Slobodkin, N. R.: A Fifth Route to 1, 2, 3-Triphenylazulene. J. Organ. Chem. (USA) 25, 273 (1960).

    CAS  Google Scholar 

  192. Šorm, F., V. Beneš ová und V. Herout: Über Terpene. LIV. Über die Struktur des Lactarazulens und Lactaroviolins. Collect. Czech. Chem. Commun. 19, 357 (1954).

    Google Scholar 

  193. Šorm, F., V. BenešOvá, J. KrupiÍka, V. Šneberk, L. Dolejš, V. Herout and J. Sicher: The Structure of Lactaroviolin. Chem. and Ind. 1954, 1511.

    Google Scholar 

  194. Šorm, F., L. Dolejš, O. Knessl and J. Plíva: On Terpenes. XVI. On a Bicyclic Sesquiterpene and a new Azulene from the Oil of Pogostemon patchouli P. Collect. Czech. Chem. Commun. 15, 82 (1950).

    Google Scholar 

  195. Šorm, F., L. Novotnx00Fd; and V. Herout: A Further Chamazulene Precursor: The Bitter Principle of Artemisia absinthium L. Chem. and Ind. 1955, 569.

    Google Scholar 

  196. Šorm, F., M. Souchý and V. Herout: On Terpenes. C. The Structure of Ambrosin. Collect. Czech. Chem. Commun. 24, 1548 (1959).

    Google Scholar 

  197. Šorm, F. and L. UrbáNek: On Terpenes. IV. On the Constitution of Carotol. Collect. Czech. Chem. Commun. 13, 49 (1948).

    Google Scholar 

  198. —: On Terpenes. VI. On the Constitution of Carotol, II. Collect. Czech. Chem. Commun. 13, 420 (1948).

    Google Scholar 

  199. Šorm, F., F. Vonášek and V. Herout: On Terpenes. VII, On a New Coloured Hydrocarbon from the Oil of Wormwood (Artemisia absinthium L.). Collect. Czech. Chem. Commun. 14, 91 (1949).

    Google Scholar 

  200. Stahl, E.: Über das Cham-Azulen und dessen Vorstufen, II. Mitt.: Cham-Azulencarbonsäure aus Kamille. Chem. Ber. 87, 505 (1954).

    CAS  Google Scholar 

  201. —: ÜBer Das Cham-Azulen und Dessen Vorstufen, Iii. Mitt.: Zur Konstitution der Cham-Azulencarbonsäure. Chem. Ber. 87, 1626 (1954).

    CAS  Google Scholar 

  202. Steele, J. W., J. B. Stenlake and W. D. Williams: The Chemistry of the Aristolochia Species. Part IV. The Structure of Aristolactone. J. Chem. Soc. (London) 1959, 3289.

    Google Scholar 

  203. Stepanow, F. N. und N. A. Aldanowa: Polymethin-Farbstoffe der Azulen-Reihe. Angew. Chem. 71, 125 (1959).

    Google Scholar 

  204. —: Novie proizvodnie azulena. (A New Preparation of Azulene.) Zhur. Obshchei Khimii 29, 339 (1959).

    Google Scholar 

  205. Suchý, M: On Terpenes. XCV. The Constitution of Two Alkylchamazulenes. Collect. Czech. Chem. Commun. 24, 1303 (1959); Chem. Listy 52, 2099 (1958).

    Google Scholar 

  206. Suchý, M., V. BenešOvá, V. Herout and F. Šorm: Contribution on the Structure of Cnicin, the Bitter Principle from Cnicus benedictus L. Tetrahedron Letters 1959, No. 10, 5.

    Google Scholar 

  207. Suchý, M., V. Herout and F. Šorm: On Terpenes. LXVIII. Formation of Two Tetraalkylazulenes in the Working up of Wormwood. Collect. Czech. Chem. Commun. 21, 477 (1956); Chem. Listy 49, 1870 (1955).

    Google Scholar 

  208. —Cnicin: A New Guaianolide-Type Lactone. Chem. and Ind. 1959, 517.

    Google Scholar 

  209. F. Šorm —: On Terpenes. CVI. On Hydrogénation Products of Cynaropicrin, the Bitter Principle of Artichoke (Cynara scolymus L.). Collect. Czech. Chem. Commun. 25, 507 (1960).

    Google Scholar 

  210. F. Šorm —: On Terpenes. CXVI. Structure of Cynaropicrin. Coll. Czech. Chem. Commun. 25, 2777 (1960).

    Google Scholar 

  211. Sutherland, M. D.: Structure of the Terpenoid Geijerene. Chem. and Ind. 1959, 1220.

    Google Scholar 

  212. Sýkora, V., V. Herout and F. Šorm: On Terpenes. LXIV. The Constitution of Elemol. Collect. Czech. Chem. Commun. 20, 220 (1955).

    Google Scholar 

  213. Sýkora, V., L. Novotny and F. Šorm: Constitution of Carotol and Daucol. Tetrahedron Letters 1959, No. 14, 24.

    Google Scholar 

  214. Takeda, K.: Components of the Root of Lindera strychnifolia VILL. VI. Structure of Linderene. Pharm. Bull. Japan I, 244 (1953).

    Google Scholar 

  215. Takeda, K. and H. Minato: Absolute Configuration of Guaiol. Tetrahedron Letters 1960, No. 22, 33.

    Google Scholar 

  216. Takada, K. and W. Nagata: Components of the Root of Lindera slrychni-folia VILL. V. Azulenes Isolated from Linderene by Zinc-Dust Distillation. Pharm. Bull. Japan I, 164 (1953).

    Google Scholar 

  217. Tilney-Bassett, J. F. and W. A. Waters: The Substitution of Azulene by Benzyl Radicals. J. Chem. Soc. (London) 1959, 3123.

    Google Scholar 

  218. Treibs, W.: Über bi-und polycyclische Azulene. XII. Das Germacrol, ein azulenbildendes Sesquiterpen-oxyd aus Geraniumöl. Liebigs Ann. Chem. 576, 116 (1952).

    CAS  Google Scholar 

  219. —: Über elektrophile Substitutionen am Azulen. Naturwiss. 45, 336 (1958).

    Google Scholar 

  220. —: Über bi-und polycyclische Azulene. XL. Azulenglyoxylsäuren und Azulencarbonsäuren, ihre Darstellung und Reduktion mit Lithiumalanat. Chem. Ber. 92, 2152 (1959).

    Google Scholar 

  221. —: Über substituierende und zyklisierende Malonylierung ohne Katalysatoren. Naturwiss. 47, 179 (1960).

    CAS  Google Scholar 

  222. Treibs, W. und H.-M. Barchet: Über bi-und polycyclische Azulene. IV. Mitt.: Das Aromadendren, sein chemischer Bau und seine Überführung in 5 Azulene. Liebigs Ann. Chem. 566, 89 (1950).

    CAS  Google Scholar 

  223. Treibs, W. und K. Gründel: Über bi-und polycyclische Azulene, XXX. Synthese von siliciumhaltigen Azulenen. Chem. Ber. 91, 143 (1958).

    CAS  Google Scholar 

  224. Treibs, W., J. Hiebsch und H. J. Neupert: Über bi-und polycyclische Azulene, XXXVIII. Synthesen von Azulencarbonsäure-nitrilen. Chem. Ber. 92, 606 (1959).

    CAS  Google Scholar 

  225. Treibs, W. und D. Merkel: Über die Gurjunene, II. α-Gurjunen. Liebigs Ann. Chem. 617, 129 (1958).

    CAS  Google Scholar 

  226. Treibs, W., M. Mühlstadt und K. D. Köher: Die Aminomethylierung der Azulene. Naturwiss. 45, 336 (1958).

    Google Scholar 

  227. Treibs, W., H. J. Neupert und J. Hiebsch: Über bi-und polycyclische Azulene, XXXVII. Synthesen und Eigenschaften von Azulen-aldehyden. Chem. Ber. 92, 141 (1959).

    CAS  Google Scholar 

  228. Treibs, W., H. J. Neupert und J. Hiebsch: Über bi-und polycyclische Azulene, XXXIX. Carboxychlorierung von Azulenen. Chem. Ber. 92, 1216 (1959).

    CAS  Google Scholar 

  229. Treibs, W. und H. Orttmann: Über Carboxylierungen mit Oxalylbromid. Naturwiss. 45, 85 (1958).

    CAS  Google Scholar 

  230. Treibs, W., G. Vollrad und M. Reimann: Über bi-und polycyclische Azulene. XLI. Die Gültigkeit der Plattnerschen Regel für 6-und 7-substituierte Azulene. Liebigs Ann. Chem. 634, III (1960).

    Google Scholar 

  231. Treibs, A., R. Zimmer-Galler und C. Jutz: Über Azulenpyrrol-methin-farbstoffe. Chem. Ber. 93, 2542 (1960).

    CAS  Google Scholar 

  232. Turner, R. B., W. R. Meador, W. V. F. Doering, L. H. Knox, J. R. Mayer and D. W. Wiley: Heats of Hydrogenation. III. Hydrogénation of Cyclo-octatetraene and of Some Seven-membered Non-benzenoid Aromatic Compounds. J. Amer. Chem. Soc. 79, 4127 (1957).

    CAS  Google Scholar 

  233. Ukita, T., M. Miyazaki and M. Hashi: Studies on Azulenes: S-Guaiazulene-aldehydes. Chem. Pharm. Bull. Japan 6, 223 (1958).

    CAS  Google Scholar 

  234. Ukita, T., M. Miyazaki and H. Watanabe: Studies on Azulenes. II. Synthesis of Polybromoazulenes. Pharm. Bull. Japan 3, 199 (1955).

    CAS  Google Scholar 

  235. Ukita, T., H. Watanabe and M. Ichige: Studies on Azulenes. VI. Synthesis of Azulenes from Hydrindenglycol Diacetate without Dehydrogenation. Pharm. Bull. Japan 5, 422 (1957).

    CAS  Google Scholar 

  236. Ukita, T., H. Watanabe and M. Miyazaki: Studies on Azulenes. I. 2-and 3-Substituted S-Guaiazulene. J. Amer. Chem. Soc. 76, 4584 (1954).

    CAS  Google Scholar 

  237. Ungnade, H. E., E. C. Hendley and W. Dunkel: Tenulin. II. Anhydro-tenulin and Pyrotenulin. J. Amer. Chem. Soc. 72, 3818 (1950).

    CAS  Google Scholar 

  238. Villiers, J. P. De: The Isolation and Structure of Geigerinin, a Guaianolide. J. Chem. Soc. (London) 1959, 2412.

    Google Scholar 

  239. Vilsmeier, A. und A. Haack: Über die Einwirkung von Halogenphosphor auf Alkyl-formanilide. Eine neue Methode zur Darstellung sekundärer und tertiärer p-Alkylamino-benzaldehyde. Ber. dtsch. chem. Ges. 60, 119 (1927).

    Google Scholar 

  240. Vivar, A. R. De and J. Romo: Constituents of Helenium mexicanum H. B. K. Chem. and Ind. 1959, 882.

    Google Scholar 

  241. Watanabe, H.: Studies on Azulenes. VII. Oxidation of Hydroazulenes with Selenium Dioxide. Pharm. Bull. Japan 5, 426 (1957).

    CAS  Google Scholar 

  242. Yoshioka, I., H. Hikino and Y. Sasaki: Studies on the Constituents of Atractylodes. III. Separation of Atractylol into Eudesmol and Hinesol. Chem. Pharm. Bull. Japan 7, 319 (1959).

    CAS  Google Scholar 

  243. Y. Sasaki —: Studies on the Constituents of Atractylodes. IV. The Structure of Hinesol (I). The Skeleton. Chem. Pharm. Bull. Japan 7, 817 (1959).

    Google Scholar 

  244. — Structure of Hinesol. Abstract, Chem. Soc. Japan Symposium Nat. Prod., Kyoto, 1960; Chem. Pharm. Bull. Japan 9, 84 (1961).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Sendai, Japan

    Tetsuo Nozoe & Shô Itô

Authors
  1. Tetsuo Nozoe
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shô Itô
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. California Institute of Technology, Pasadena, USA

    L. Zechmeister

Rights and permissions

Reprints and permissions

Copyright information

© 1961 Springer-Verlag in Vienna

About this chapter

Cite this chapter

Nozoe, T., Itô, S. (1961). Recent Advances in the Chemistry of Azulenes and Natural Hydroazulenes. In: Zechmeister, L. (eds) Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles. Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles, vol 19. Springer, Vienna. https://doi.org/10.1007/978-3-7091-7156-1_2

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-7156-1_2

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-7158-5

  • Online ISBN: 978-3-7091-7156-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation