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Introduction

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The Nitrile Oxides

Part of the book series: Organische Chemie in Einzeldarstellungen ((ORGCHEMIE,volume 13))

Abstract

Definition. Nitrile oxides, RCNO, are organic compounds which contain the monovalent functional group -CNO bound directly to a carbon atom of the organic moiety of the molecule. Only the first member of this series, fulminic acid or formonitrile oxide, H-CNO is an exception; mainly for this reason its chemistry differs in some respects from that of its homologs.

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References

  1. Beck, W.: Angew. Chem. 75, 872 (1963).

    Article  Google Scholar 

  2. Beck, W.: Z. Naturforsch. 17b, 130 (1962).

    Google Scholar 

  3. Beck, W., Lux, F.: Chem. Ber. 95, 1683 (1962).

    Article  CAS  Google Scholar 

  4. Quilico, A.: The chemistry of heterocyclic compounds (ed. A. Weissberger), vol. XVII, chap.: Isoxazoles and related compounds, p. 1–176. New York: Interscience 1962.

    Google Scholar 

  5. Behr, L. C.: The chemistry of heterocyclic compounds (ed. A. Weissberger), vol. XVII, chap.: Furazans, p. 283–320. New York: Interscience 1962.

    Google Scholar 

  6. Barnes, R. A.: Heterocyclic compounds (ed. R.C. Elderfield), vol. 5, chap.: Isoza-zoles, p. 452–482. New York: J. Wiley & Sons 1957.

    Google Scholar 

  7. Boyer, J. H.: Heterocyclic compounds (ed. R. C. Elderfield), vol. 7, chap.: Oxadiazoles, p. 462–508. New York: J. Wiley & Sons 1961.

    Google Scholar 

  8. Grundmann, C.: Methoden der organischen Chemie, 4th ed. (ed. E. Müller), vol. 10/3, chap.: Methoden zur Herstellung und Umwandlung von Nitriloxiden, p. 837–870. Stuttgart: G. Thieme 1965.

    Google Scholar 

  9. Grundmann, C.: Chemistry of nitrile oxides. Fortschr. Chem. Forsch. 7, 62–127 (1966).

    Article  CAS  Google Scholar 

  10. Grundmann, C.: The chemistry of the cyano group (ed. Z. Rappoport), chap.: Nitrile oxides, p. 791–851. New York: Interscience 1970.

    Google Scholar 

  11. Grundmann, C.: Syntheses of heterocyclic compounds with the aid of nitrile oxides. Synthesis, 344–359 (1970).

    Google Scholar 

  12. Quilico, A.: Advances in nitrile oxides chemistry. Experientia 26, 1169–1183 (1970).

    Article  CAS  Google Scholar 

  13. Feldhaus H: Nitrocellulose 4, 83 (1933).-Kirk-Othmer: Encyclopedia of chemical technology, vol. 6, p. 10. New York: Interscience Encyclopedia 1951.

    Google Scholar 

  14. Howard, E.: Phil. Trans. Roy. Soc. London 204 (1800).

    Google Scholar 

  15. Liebig, J., Gay-Lussac, J. L.: Ann. Chim. Phys. [2] 25, 285 (1824).

    Google Scholar 

  16. Hodgkinson, W. R.: J. Soc. Chem. Ind. 37, 190T (1918);-Chem. Abstr. 12, 2687 (1918).

    Google Scholar 

  17. Bergfeld, L.: Z. ges. Schiess-u. Sprengstoffw. 37, 84 (1942);-Chem. Abstr. 37, 55925 (1943).

    CAS  Google Scholar 

  18. Liebig, J., Gay-Lussac, J. L.: Ann. Chim. Phys. [2] 25, 303 (1824).

    Google Scholar 

  19. Liebig, J.: Ann. Chim. Phys. [2]24, 294 (1823).-Wöhler, F.: Ann. Chim. Phys. [2] 27, 196(1824).

    Google Scholar 

  20. Kékulé, A.: Ann. Chem. 101, 200 (1857).

    Article  Google Scholar 

  21. Kékulé, A.: Ann. Chem. 105, 281 (1858).

    Google Scholar 

  22. Griess, P.: Ann. Chem., Suppl. 1, 104 (1861).

    Google Scholar 

  23. Carstanjen, E., Ehrenberg, A.: J. Prakt. Chem. [2]25, 232 (1882).-Ehrenberg, A. J. Prakt. Chem. [2] 30, 41 (1884).

    Article  Google Scholar 

  24. Steiner, A.: Ber. 16, 1484; 2419 (1883).

    Article  Google Scholar 

  25. Divers, E., Kawakita, M.: J. Chem. Soc. 45, 13 (1884).

    Article  CAS  Google Scholar 

  26. Scholl, R.: Ber. 23, 3505 (1890).-Holleman, A. F.; Ber. 23, 3742 (1890).

    Article  Google Scholar 

  27. Divers, E.: J. Chem. Soc. 45, 19 (1884).

    CAS  Google Scholar 

  28. Nef, J. U.: Ann. Chem. 280, 291 (1894).

    Google Scholar 

  29. Nef, J. U.: Ann. Chem. 280, 263 (1894).

    CAS  Google Scholar 

  30. Wieland, H.: Ber. 40, 418 (1907); 43, 3362 (1910).

    Article  CAS  Google Scholar 

  31. Wieland, H.: Ber. 42, 803, 820 (1909).

    Article  CAS  Google Scholar 

  32. Wöhler, L.: Ber. 38, 1356 (1905).

    Google Scholar 

  33. Lindemann, H., Wiegrebe, L.: Ber. 63, 1650 (1930).

    Google Scholar 

  34. Ley, H., Kissel, M.: Ber. 32, 1357 (1899).

    Article  Google Scholar 

  35. Palazzo, F. C: Atti Accad. Lincei [5]21V, 713 (1912).

    Google Scholar 

  36. Klages, F.: Naturwissenschaften 30, 357 (1942). 23b Quilico, A., Speroni, G.: Gazz. Chim. Ital. 76, 148 (1946).

    Article  Google Scholar 

  37. Pauling, L., Hendricks, S.B.: J. Am. Chem. Soc. 48, 641 (1926).

    Article  CAS  Google Scholar 

  38. Huisgen, R.: Proc. Chem. Soc. 357 (1961).

    Google Scholar 

  39. Beck, W., Schuierer, E., Feldl, K.: Angew. Chem. 77, 722 (1965).

    Article  Google Scholar 

  40. Gabriel, S., Koppe, M.: Ber. 19, 1145 (1886).

    Article  Google Scholar 

  41. Caramella, P., Grünanger, P.: Unpublished.

    Google Scholar 

  42. Werner, A., Buss, H.: Ber. 27, 2193 (1894).

    Article  Google Scholar 

  43. Wieland, H.: Ber. 40, 1667 (1907).

    Article  CAS  Google Scholar 

  44. Auwers, K. v.: Ber. 61, 1041 (1928).

    Google Scholar 

  45. Weygand, C., Bauer, E.: Ann. Chem. 459, 123 (1927).

    CAS  Google Scholar 

  46. Grundmann, C., Dean, J.M.: Angew. Chem. 76, 682 (1964).

    Article  CAS  Google Scholar 

  47. Wieland, H.: Ber. 40, 1667 (1907).

    Article  CAS  Google Scholar 

  48. Wieland, H.: Die Knallsäure. Sammlung chemischer und chemisch-technischer Vorträge (ed. F. B. Ahrens), vol. 14, p. 385–461. Stuttgart: F. Enke 1909.

    Google Scholar 

  49. Auwers, K. v.: Ber. 61, 1041 (1928).

    Google Scholar 

  50. Pauling, L., Hendricks, S.B.: J. Am. Chem. Soc. 48, 641 (1926).

    Article  CAS  Google Scholar 

  51. Huisgen, R.: Proc. Chem. Soc. 357 (1961).

    Google Scholar 

  52. Huisgen, R.: Angew. Chem. 75, 604 (1963).

    Article  CAS  Google Scholar 

  53. Quilico, A., Speroni, G.: Gazz. Chim. Ital. 76, 148 (1946).-Quilico, A., Stagno d’Alcotres, G., Grünanger, P.: Gazz.Chim. Ital. 80, 479 (1950); Nature 166, 226 (1950).

    CAS  Google Scholar 

  54. Steiner, A.: Ber. 16, 1484 (1883). Carstanjen, E., Ehrenberg, A.: J. Prakt. Chem. [2] 25, 232 (1882).

    Article  Google Scholar 

  55. Werner, A., Buss, H.: Ber. 27, 2193 (1894).

    Article  Google Scholar 

  56. Grundmann, C., Frommeld, H. D.: J. Org. Chem. 31, 157 (1966).

    Article  CAS  Google Scholar 

  57. McGrath, W. D., Morrow, T.: Nature 203, 619 (1964); 204, 988 (1964).

    Article  CAS  Google Scholar 

  58. Olivieri-Mandalá, E.: Gazz. Chim. Ital. 521, 107 (1922).

    Google Scholar 

  59. Radziszewski, B.: Ber. 18, 355 (1885).-McMaster, L., Langreck, F. B.: J. Am. Chem. Soc. 39, 103 (1917).

    Article  Google Scholar 

  60. Biddle, H. C.: Ann. Chem. 310, 19 (1900); Ber. 38, 3858 (1905).

    Google Scholar 

  61. Beck, W: Private communication.

    Google Scholar 

  62. Ehrenberg, A.: J. prakt. Chem. [2]32, 230 (1885).

    Article  Google Scholar 

  63. Wähler, L.: Ber. 38, 1351 (1905).

    Article  Google Scholar 

  64. Wähler, L., Weber, A.: Ber. 62, 2742 (1929).

    Google Scholar 

  65. Wieland, H.: Ber. 42, 803 (1909).

    Article  CAS  Google Scholar 

  66. Grundmann, C., Mini, V., Dean, J.M., Frommeid, H.-D.: Ann. Chem. 687, 191(1965).

    Google Scholar 

  67. Eloy, F.: Private communication.

    Google Scholar 

  68. Grundmann, C.: Unpublished.

    Google Scholar 

  69. Beltrame, P., Comotti, A., Veglio, C.: Chem. Commun. 996 (1967).

    Google Scholar 

  70. Dondoni, A., Mangini, A., Ghersetti, S.: Tetrahedron Letters 4789 (1966).

    Google Scholar 

  71. Grundmann, C., Frommeld, H.-D.: J. Org. Chem. 31, 4235 (1966).

    Article  CAS  Google Scholar 

  72. Eloy, F.: Bull. Soc. Chim. Beiges 73, 639 (1964).-Iwakura, Y., Akiyama, M., Shiraishi, S.: Bull. Chem. Soc. Japan 37, 767 (1964).-Overberger, C.G., Fujimoto, S.: J. Polymer Sci. C4161 (1968).

    Article  CAS  Google Scholar 

  73. Ponzio, G.: Gazz. Chim. Ital. 66, 119, 123 (1936).

    Google Scholar 

  74. Grundmann, C., Dean, J.M.: Angew. Chem. 76, 682 (1964); J. Org. Chem. 30, 2809 (1965).

    Article  CAS  Google Scholar 

  75. Grundmann, C., Richter, R.: J. Org. Chem. 32, 2308 (1967); 33, 476 (1968).

    Article  CAS  Google Scholar 

  76. Grundmann, C., Datta, S. K.: J. Org. Chem. 34, 2016 (1969).

    Article  CAS  Google Scholar 

  77. Wieland, H., Rosenfeld, B.: Ann. Chem. 484, 236 (1930).

    CAS  Google Scholar 

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Grundmann, C., Grünanger, P. (1971). Introduction. In: The Nitrile Oxides. Organische Chemie in Einzeldarstellungen, vol 13. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-99991-8_1

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  • DOI: https://doi.org/10.1007/978-3-642-99991-8_1

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