Skip to main content
SpringerLink
Log in

Photoaddition and Photocyclization Processes of Aromatic Compounds

  • Chapter
Synthetic Organic Photochemistry

Abstract

The present intensive interest in the photochemistry of aromatic systems has its origins in observations reported in the late 1950s that benzene, contrary to the widely held opinion of the time, was photolabile and would undergo both isomerization(1) and addition(2) reactions when subjected to ultraviolet irradiation. From this time there has developed an awareness that the photochemical reactions of arenes have enormous potential both for the synthesis of novel compounds and the provision of convenient and versatile routes to systems, the thermal synthesis of which is, for one reason or another, troublesome. Photoisomerization reactions of arenes leading to benzvalenes, bicyclo[2.2.0]hexadienes, prismanes, and fulvenes have, for most systems, little synthetic application largely because of their low quantum and chemical yields of formation. This area of aromatic photochemistry has recently been reviewed,(3–5) and the synthetic and mechanistic aspects of the photosubstitution reactions of arenes have been similarly treated.(6)

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover 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.

References

  1. J. M. Blair and D. Bryce-Smith, The photoisomerisation of benzene to fulvene, Proc. Chem. Soc. 1957, 287–288.

    Google Scholar 

  2. H. J. F. Angus and D. Bryce-Smith. Addition of maleic anhydride to benzene, Proc. Chem. Soc. 1959, 326–327.

    Google Scholar 

  3. D. Bryce-Smith and A. Gilbert, The organic photochemistry of benzene I. Tetrahedron 32, 1309–1327 (1976).

    Article  CAS  Google Scholar 

  4. D. Bryce-Smith and A. Gilbert, in: Rearrangements in Ground and Excited States (P. de Mayo, ed.). Vol. 3, pp. 349–379, Academic Press, New York (1980).

    Google Scholar 

  5. G. Kaupp. Photochemical rearrangements and fragmentations of benzene derivatives and annelated arenes. Angew. Chem. Int. Ed. 19, 243–275 (1980).

    Article  Google Scholar 

  6. See for example E. Havinga and H. Cornelisse, Aromatic photosubstitution reactions, Pure Appl. Chem. 47, 1–10 (1976).

    Article  CAS  Google Scholar 

  7. A. Gilbert, in: Photochemistry (D. Bryce-Smith. ed), Specialist Periodical Reports, Vols. 1–10. The Royal Society of Chemistry, London (1970–1979) and J. D. Coyle. Vols. II–13 (1981–82).

    Google Scholar 

  8. D. Bryce-Smith and A. Gilbert, The organic photochemistry of benzene II. Tetrahedron 33, 2459–2489 (1977).

    Article  CAS  Google Scholar 

  9. A. Gilbert, The inter- and intramolecular photocycloaddition of ethylenes to aromatic compounds. Pure Appl. Chem. 52, 2669–2682 (1980).

    Article  CAS  Google Scholar 

  10. T. Wagner-Jauregg. Thermische und photochemische additionen von dienophilen an arene und deren vinyloge und heteroanaloge. Synthesis 1980. 165–214.

    Google Scholar 

  11. D. Bryce-Smith. B. E. Foulger, and A. Gilbert, Photoaddition of allenes to benzene. J. Chem. Soc. Chem. Commun. 1972, 664–665.

    Google Scholar 

  12. H. D. Scharf, H. Leismann, W. Erb, H. W. Gaidetzka, and J. Aretz, The photocycloaddilion of dichlorovinylene carbonate to benzene and naphthalene. Pure Appl. Chem. 41, 581–600 (1975).

    Article  CAS  Google Scholar 

  13. G. Kaupp, Photo-Diels-Alder Reaktionen mit anthracen, Justus Liebig’s Ann. Chem. 2, 254–275 (1977).

    Article  Google Scholar 

  14. D. Bryce-Smith, B E. Foulger, J. Forrester, A. Gilbert, B. H. Orger, and H. M. Tyrrell, The photoaddition of ethylenic hydrocarbons to benzene, J. Chem. Soc. Perkin Trans. I 1980, 55–71.

    Google Scholar 

  15. A. Gilbert, G. N. Taylor, and M. W. bin Samsudin, The photocycloaddilion of enol ethers to benzene. J. Chem. Soc. Perkin Trans. I 1980, 869–876

    Google Scholar 

  16. D. Bryce-Smith, Orbital symmetry relationship for thermal and photochemical concerted cycloadditions to the benzene ring, Chem. Commun. 1969, 806–809.

    Google Scholar 

  17. Sec for example H-G. Henne and W. Hartmann. Photochemical cycloaddition of benzene to vinylene carbonatc. Angew. Chem. Int. Ed. 14, 698–699 (1975).

    Google Scholar 

  18. J. Mattay, H. Leismann, and H-D. Scharf. Photochemische cycloaddition von benzol an 1,3-dioxole und 1,4-dioxen. Teil 1: praparative ergebnisse, Chem. Ber. 112, 577–599 (1979); J. Mattay, J. Runsink, H. Leismann. and H-D Scharf. Photochemical cycloaddition of olefins to aromatic compounds. Tetrahedron Lett. 23, 4919–4922 (1982).

    Google Scholar 

  19. M. Demuth and K. Schaffner, Photochemically prepared building blocks for enantiospecific total synthesis of cyclopentanoid natural products, Angew. Chem. Int. Ed. Engl. 21, 820– 836 (1982).

    Google Scholar 

  20. A. Gilbert and M. W. bin Samsudin, The photocycloaddilion of vinyl acetate to benzene and its simple derivatives. J. Chem. Soc. Perkin Trans. I 1980, 1118–1123.

    Google Scholar 

  21. A. Gilbert and P. Yianni, Regio- and stereo-selectivities of the ortho and meta photocycloaddition reactions of ethylenes to benzene and its simple derivatives. Tetrahedron 37, 3275–3283 (1981).

    Article  CAS  Google Scholar 

  22. P. A. Wender and G. B. Dreyer. Synthetic studies on arene-olefin cycloadditions. Total synthesis of (±)-isoiridomyrmecin, Tetrahedron Letters 24, 4543–4546 (1983).

    Google Scholar 

  23. P. A. Wender and G. B. Dreyer. Synthetic studies on arene–olefin cycloadditions. Total synthesis of (±)-modhephene. J. Am. Chem. Soc. 104, 5805–5807 (1982).

    Article  CAS  Google Scholar 

  24. J. Cornelisse, V. Y. Merritt. and R. Srinivasan. Photochemical 1,3-addition of benzene to olefins, J. Am. Chem. Soc. 95, 6197–6203 (1973); J. A. Ors and R. Srinivasan, Photochemical 1,3–addition of anisole to olefins. Synthetic aspects. J. Org. Chem. 42, 1321–1327 (1977).

    Google Scholar 

  25. M. G. B. Drew, A. Gilbert, P. Heath, A. J. Mitchell, and P. W. Rodwell, Substituent directed meta photocycloaddition of trans 1,2-dichlorocthene to benzonitrile. J. Chem. Soc. Chem. Comm. 1983, 750–751.

    Google Scholar 

  26. E. Grovenstein, D. V. Rao, and J. W. Taylor, The structure and stereochemistry of the photochemical adduct of benzene with maleic anhydride, J. Am. Chem. Soc. 83, 1705–1711. (1961): D. Bryce-Smith and J. E. Lodge. Mechanism of the photoaddition of maleic anhydride to benzene, J. Chem. Soc. 1962, 2675–2680.

    Google Scholar 

  27. G. O. Schenck and R. Steinmetz. Neuartige durch benzophenon photosensibilisierte additionen von maleinsaureanhydrid an benzol und ardere aromaten. Tetrahedron Lett. 21, 1–8 (1960); W. M. Hardham and G. S. Hammond, Mechanisms of photochemical reactions in solution: addition of maleic anhydride to benzene. J. Am. Chem. Soc. 89, 3200–3205 (1967).

    Article  Google Scholar 

  28. W. Hartmann, H-G. Heine, and L Schrader. Synthese und einige einigeschaften von bicyclo [4.2.0]-2,4-dien-exo-7,8-dicarbonsaureanhydrid, Tetrahedron Lett. 1974, 883–886, and 3101–3104: D. Bryce-Smith. R. Deshpande. and A. Gilbert. Mechanism of the photoaddition of maleic anhydride to benzene, Tetrahedron Lett. 1975, 1627–1630.

    Google Scholar 

  29. D. Bryce-Smith, Photoaddition and photoisomerisation reactions of the benzene ring. Pure Appl. Chem. 16. 47–63 (1968).

    Article  CAS  Google Scholar 

  30. D. Bryce-Smith and A. Gilbert. Temperature dependence of orientation in the photosensitised addition of maleic anhydride to methyl benzenes. Chem. Commun. 1968, 19–21.

    Google Scholar 

  31. D. Bryce-Smith. A. Gilbert, and B. Vickery, A simple high-yield preparation of the benzene maleic anhydride adduct, Chem. Ind. 1962, 2060.

    Google Scholar 

  32. D. Bryce-Smith and M. A. Hems. Photoaddition of nialamide and some N-substituted nialamides to benzene. Tetrahedron Lett. 1966, 1895–1899.

    Google Scholar 

  33. J. S. Bradshaw, The photosensitised addition of malcimide to benzene in the absence of a charge-transfer complex. Tetrahedron Lett. 1966, 2039–2042.

    Google Scholar 

  34. Y. Musa and M. P. Stevens, Synthesis of polyimides by photoaddition of bismaleimidcs to benzene. J. Polymer. Sci. 10, 319–327. 1093–1096 (1972).

    Google Scholar 

  35. M. P. Stevens. Photopolymerisation and crosslinking by the benzene-bimaleimide photoaddition reaction, Am. Chem. Soc. Symp. Ser. 25, 64–75 (1976).

    CAS  Google Scholar 

  36. D. Bryce-Smith. Photoaddition to the benzene ring. Pure Appl. Chem. 34, 193–212 (1973).

    Article  CAS  Google Scholar 

  37. V. Sh. Shaikhrazieva, E. V. Tal’Vinskii, L. M. Khalivov, and G. A. Tolstikov, Photoinduced reactions of dichloromaleimide with some aromatic compounds, Izv. Akad. Nauk. SSSR, Ser. Khim. 1979, 401–404 [Chem. Abs. 90, 203801 (1979)].

    Google Scholar 

  38. D. Bryce-Smith, A. Gilbert, and B. Halton. Photoaddition of malcimide to anisole. J. Chem. Soc Perkin I 1978, 1172–1175.

    Google Scholar 

  39. N. Al-Jalal and A. Gilbert, Competitive arene substitution and ortho cycloaddition in the photochemical reactions of methoxybenzene-acrylonitrile systems, J. Chem. Rex. 1983, 266– 267.

    Google Scholar 

  40. T. S. Cantrell. Photochemical cycloadditions of benzonitrile to alkenes. Factors controlling the site of addition, J. Am. Chem. Soc. 42, 4238–4245 (1977).

    CAS  Google Scholar 

  41. J. L. Charlton and P. de Mayo. The Photocycloaddition of nitrobenzene to alkenes, Can. J. Chem. 46, 1041–1042 (1968).

    Article  CAS  Google Scholar 

  42. B. Sket and M. Zupan. Stereospecific 2 + 2 photoaddition of indene and 1.2-dihydronaphthalene to hexafluorobcnzene. J. Chem. Soc. Chem. Commun. 1976, 1053; Stereochcmistry of the 2 + 2 photoaddition of norbornadiene to hexafluorobenzene. Tetrahedron Lett. 1977, 2811–2814.

    Google Scholar 

  43. D. Bryce-Smith, A. Gilbert, B. H. Orger. and P. J. Twitchett. Photoaddition of ethylenes and acetylenes to hexafluorobenzene, J. Chem. Soc. Perkin Trans. I 1978, 232–243.

    Google Scholar 

  44. D. Bryce-Smith, A. Gilbert, and B. H. Orger, Photochemical 1.3-cycloaddition of olefins to aromatic compounds. Chem. Commun. 1966, 512–514; Y. Inoue, K Nishida, K. Ishibe. T. Hakushi, and N. J. Turro. Photochemical reaction of naphthalene with cis- and trans- cyclooctene, Chem. Lett. 1982, 471–474.

    Google Scholar 

  45. J. J. McCullough, W. K. MacInnis. C. J. L. Lock, and R. Faggiani, Naphthonitrile-alkene exciplexes. Comparison of bimolecular and bichromophoric cases: Effects of linking on fluorescence and photochemistry, J. Amer. Chem. Soc. 104, 4644–4658 (1982). K. Mizuno, C. Pac, and H. Sakurai, Stereospecific photocycloaddition of cis and trans-1-methoxypropenes to 2-naphthonitrile, J. Org. Chem. 42, 3313–3315 (1977).

    Article  Google Scholar 

  46. D. R. Arnold, P. C. Wong, A. J. Maroulis, and T. S. Cameron. The photoaddition of olefins to cyano aromatic compounds in polar solvents. Pure Appl. Chem. 52, 2609–2619 (1980).

    Article  CAS  Google Scholar 

  47. N. C. Yang. B. Kim. W. Chiang, and T. Hamada. Photochemical synthesis of 1-azetines, J. Chem. Soc. Chem. Commun. 1976, 729–730.

    Google Scholar 

  48. M. Yasuda, C. Pac. and H. Sakurai, Photorcactions of 1–cyanonaphthalene with indene in various solvents. Bull. Chem. Soc. Jpn. 55, 502–508 (1980).

    Article  Google Scholar 

  49. R. A. Caldwell and D. Creed. Exiplex intermediates in 2 + 2 photocycloaddilions. Acc. Chem. Res. 13, 45–50 (1980).

    Article  CAS  Google Scholar 

  50. W. Reid, H. Schinzel. A H. Schmidt. W. Schuckmann, and H. Fuess, Über die sensibilisierte [2 + 2]-photocycloaddilion von dichlorovinylencarbonat an phenanthren. Chem. Ber. 113, 255–260 (1980).

    Article  Google Scholar 

  51. R. A. Caldwell and T-S. Maw, The effect of multiplicity on regiochemistry of (2 + 2) photocycloaddition of 3.9-dicyanophenanthrene to β-methylstyrene. J. Photochem. 11, 165–171 (1979).

    Article  CAS  Google Scholar 

  52. M G. Barlow, D. E Brown, and R N Haszeldine. The photochemical addition of ethylene to pcntafluoropyridine. Formation of 1:1 and 2:1 adducts. J. Chem. Soc. Perkin Trans. I 1978, 363–365; B Sket, N. Zupancic. and M. Zupan. Regio- and stereospecific [2 + 2] photoaddition of cycloalkenes to pentafluoropyridine, J. Org. Chem. 47, 4462–4464 (1982); M G. Barlow, D. E. Brown, and R. N. Haszeldine, Photochemical addition of 2-butyne to pentafluoropyridine to give 1:1 and 2:1 adducts. J. Fluorine Chem. 20, 743–750 (1982).

    Google Scholar 

  53. I. Saito, K. Kanehira, K. Shimozono, and T. Matsuura, Photoaddition of 2-cyanopyridine to olefins. Tetrahedron Lett. 1980, 2737–2740.

    Google Scholar 

  54. P. Hrdlovič, L. Záhumensky, I. Lukác, and P. Sláma. Photochemical addition of maleic anhydride derivatives to benzene and polystyrene sensitised by low and high molecular weight carbonyls. J. Polym. Sci. Polym. Chem. Ed. 16, 877–888 1978 )

    Article  Google Scholar 

  55. D. Bryce-Smith and J. E. Lodge, Preparation of cyclooctatetraenes by the photoaddition of acetylenes to benzene. Proc. Chem. Soc. 1961, 333–334; J. Chem. Soc. 1963, 695–701; E. Gronenstein and D. V. Rao, Photochcmical reaction of benzene with dimethyl acetylene dicarboxylate. Tetrahedron Lett. 1961, 148–150.

    Google Scholar 

  56. G. L. Grunewald and J. M. Grindel, Carbomethoxycyclo-octatetraene synthesis. Org. Photochem. Synth. 2, 20–22 (1976); L A. Paquette and R S. Beckley. 1.2-Di-Dicarbomethoxycyclooctatetraene synthesis. Org. Photochem. Synth. 2, 45 46 (1976).

    Google Scholar 

  57. A. H. A. Tinnemans and D. C. Neckers. Photoaddition of methyl phenylpropiolate to benzene, J. Am. Chem. Soc. 99, 6459–6460 (1977); Tetrahedron Lett. 1978, 1713–1716; Y. Hanzawa and L. Paquette, Photochemical preparation of 5-tert-butyl-4-methoxycarbonyltetracyclo[3.3.0.02,403,6]oct-7-ene. Synthesis 8, 661–662 (1982).

    Google Scholar 

  58. D Bryce-Smith, A. Gilbert, and J. Grzonka, Photoaddition of acetylenes to benzene. Chem. Commun. 1970, 498–499.

    Google Scholar 

  59. J. Grzonka, The Photoaddition of acetylenes to benzene and benzene derivatives, Ph.D thesis. Reading (1973).

    Google Scholar 

  60. B. Sket and M. Zupan, 2 + 2 Photoaddition of acetylenes to hexafluorobenzene. J. Am. Chem. Soc. 99, 3504–3505 (1977).

    Article  CAS  Google Scholar 

  61. T. Teitei and D. Wells. Novel Photochemical 1,3-addition of trimesic acid esters to diphenylacetylene. Tetrahedron Lett. 1975, 2299–2302.

    Google Scholar 

  62. E. Grovenstein, T. C. Campbell, and T. Shibata. Photochemical reactions of dimethyl acetylenedicarboxylate with benzene and naphthalene, J. Org. Chem. 34, 2418–2428 (1969).

    Article  CAS  Google Scholar 

  63. G. Sagowdz, P. J. Collin, and W. H. F. Sasse. The formation of benzxisemibullvalene derivatives in the photoaddition of diphenylacetylene to methyl 2-naphthoate. Austral J. Chem. 26, 147–171 (1973).

    Article  Google Scholar 

  64. T. Teitei, D. Wells, and W. H. F. Sasse, Synthesis and reactions of 8b-methoxy- and 4,8b-dimethoxydihydrocyclobuta [a] naphthalene. Austral. J. Chem. 28, 571–579 (1975) and references therein.

    Google Scholar 

  65. M. Sindler-Kulyk and D. C. Neckers. Photochemical reactions of 3-phenyl-l,2-benzoisothiazole with alkynes, J. Org. Chem. 48, 1275–1281 (1983).

    Article  CAS  Google Scholar 

  66. P D. Davis, D. C. Neckers, and J R. Blount, Photocycloaddition of dimethyl acetylenedicarboxylate to 1,3-dimethylindole, J. Org. Chem. 45, 462–471 (1980); P. D. Davis and D. C. Neckers. Photocycloaddition of dimethyl acetylenedicarboxylate to activated indoles. J. Org. Chem. 45, 456–462 (1980).

    Article  CAS  Google Scholar 

  67. K. Kraft and G. Koltzenburg, Photochemische reaktionen von aromaten mit konjugierten dienen. Neue addukte des benzols an butadiene-(1.3), Tetrahedron Lett. 1967, 4357–4362; 4723–4728.

    Article  Google Scholar 

  68. H. P. Locffler. Synthese von bicyclo[4.2.2]deca-2.4.7.9-tetraen. Tetrahedron Lett. 1974, 787–788.

    Google Scholar 

  69. J. Ipaktschi and M. N. Iqbal. Photoaddition of isoprcne to benzene: synthesis of 3-methylenebicyclo[4.2.2]deca-7,9-diene, Synthesis 9, 633 (1977).

    Article  Google Scholar 

  70. N. C. Yang and J. Libman. Photochemical additions of 1.3-dienes to benzene. Tetrahedron Lett. 1973, 1409–1412.

    Google Scholar 

  71. J. C. Berridge, J. Forrester, B. E. Foulger, and A. Gilbert, The photochemical reactions of benzene with 1,2-, 1,3-, and 1.4-dienes, J. Chem. Soc. Perkin Trans. I 1980, 2425–2434.

    Google Scholar 

  72. K. T. Mak, J. Srinivasachar, and N. C. Yang, Syntheses of cycloadducts of benzene and naphthalene, J. Chem. Soc. Chem. Commun. 1979, 1038–1040.

    Google Scholar 

  73. N. C. Yang, R. L. Yates, J. Masnovi, D. M. Shold, and W. Chiang. Photocycloadditions of anthracenes to conjugated polyenes. Pure Appl. Chem. 51, 173–180 (1979); G. Kaupp, H. W. Grueter. and E. Teufel. Photoadditions of anthracenes to 2.4-hexadiene and 1,3,5-cycloheptatriene, Chem. Ber. 116, 630–644 (1983).

    Article  Google Scholar 

  74. N. C. Yang and D. M. Shold. Role of cxciplexes in the photocycloaddition of 2,5-dimethylhexa-2,4-diene to anthracene. J. Chem. Soc. Chem. Commun. 1978, 978.

    Google Scholar 

  75. N. C. Yang, J. Masnovi, and W. Chiang. The role of conservation of orbital symmetry in cycloadditions of olefins to aromatic hydrocarbons, J. Am. Chem. Soc. 101, 6465–6466 (1979).

    Article  CAS  Google Scholar 

  76. See for example The Exiplex (M. Gordon and W. R. Ware, eds.), Academic Press. New York (1975). and references therein.

    Google Scholar 

  77. M. Bellas, D. Bryce-Smith, M. T. Clarke. A. Gilbert. G. Klunklin, S. Krestonosich, C. Manning, and S Wilson. The photoaddition of aliphatic amines to benzene. J. Chem. Soc. Perkin Trans. I 1977, 2571–2580.

    Google Scholar 

  78. A. Gilbert, S. Krestonish, and D. L. Westover, Photochemical reactions of substituted benzenes with aliphatic amines. J. Chem. Soc. Perkin Trans. I 1981, 295–302.

    Google Scholar 

  79. A. Gilbert and S. Krestonosich, Excited state substitution and addition reactions of aryl fluorides with aliphatic amines, J. Chem. Soc. Perkin Trans. I 1980, 1393–1399.

    Google Scholar 

  80. M. Bellas, D. Bryce-Smith, and A. Gilbert, 1,4-Photoaddition of pyrrole to benzene, Chem. Commun. 1967, 263–264; C. Manning. The photoaddition of aliphatic amines to benzene and related topics, Ph.D. thesis, Reading (1974).

    Google Scholar 

  81. J. A. Barltrop, The photoreduction of aromatic systems. Pure Appl. Chem. 33, 179–195 (1973).

    Article  CAS  Google Scholar 

  82. S. Vaidyanathan and V. Ramakrishnan, Solvent effect on the kinetics of photorcaction between anthracene and aromatic amines. Indian J. Chem. B15, 269–273 (1977).

    Google Scholar 

  83. N. C. Yang, D. M. Shold, B Kim. Photochemistry of anthracene in the presence and absence of dimethylaniline. J. Am. Chem. Soc. 98, 6587–6596 (1976); J. Saltiel, D. E. Townsend. B. D. Watson. P. Shannon, and S. L. Finson. Concerning the participation of the anthracene/N,N-dimethylaniline exciplex in anthracene photodimerisation, J. Am. Chem. Soc. 99, 884–896 (1977).

    Article  Google Scholar 

  84. D. Bradbury and J. A Barltrop, Deuterium-labelling study of the photoreduction of phenols by sodium borohydride. J. Chem. Soc. Chem. Commun. 1975, 42–843.

    Google Scholar 

  85. K. Mizuno, H. Okamoto, C. Pac. and H Sakurai, The photo-Birch reduction of aromatic hydrocarbons using sodium borohydride and 1,4-dicyanobcnzene. J. Chem. Soc. Chem. Commun. 1975, 839–840.

    Google Scholar 

  86. A. Lablache-Combier in: Eléments de Photochemie Avancée. (P. Courlot, ed.), pp. 289–471, Hermann, Paris (1972); Photochemistry of Heterocyclic Compounds (O. Buchardt. ed). Wiley-Interscience. New York (1976).

    Google Scholar 

  87. K. Kano and T. Matsuo. Photochemical reduction of pyridinium and pyridine compounds in the presence of diethylamine. Tetrahedron Lett. 1975, 1389–1392.

    Google Scholar 

  88. T. Matsuura, T. Itahara, T. Otsuki, and I. Saito. Photoreduction of 1-benzyl-3-carbamoylpyridinium chloride in aqueous ammonia. Bull. Chem. Soc. Jpn. 51, 2698–2701 (1978).

    Article  CAS  Google Scholar 

  89. T. Caronna, S. Morrocchi, and B. M. Vittimberga, Photosubstitution reactions of triethylamine with 4-cyano and 4-chloropyridine. Chim. Ind. (Milan) 60, 806–807 (1978).

    CAS  Google Scholar 

  90. S. Futamura, H. Ohta, and Y. Kamiya, Photoesterification of phcnanthridinc in carboxylic acid. Tetrahedron Lett. 1979, 4299–4302.

    Google Scholar 

  91. J. P. Desvergne, F. Chekpo, and H Bouas-Laurent, Photodimcrisation of some dichloroanthracenes in the solid state and in fluid solution, J. Chem. Soc. Perkin Trans. II 1978, 84–87.

    Google Scholar 

  92. F. C. De Schryver, N. Boens, J. Huybrechts, J. Daemen, and M. De Brackelaire. Photochemistry of bichromophoric compounds. Pure Appl. Chem. 49, 237–247 (1977).

    Article  Google Scholar 

  93. H. Bouas-Laurent, A. Catellan, and J. P. Desvergne, From anthracene photodimerisation to jaw photochromic materials and photocrowns. Pure Appl. Chem. 52, 2633–2648 (1980); H. D. Becker, On the relationship between molecular geometry and excited state reactivity. Adiabatic photorcactions involving anthracenes, Pure Appl. Chem. 54, 1589–1604 (1982).

    Article  Google Scholar 

  94. A. Castellan, J.-M. Lacoste and H. Bouas-Laurent. Photocyclomerisation and fluorescence of bis-9-anthrylmethyl ethers, J. Chem. Soc. Perkin Trans. II 1979, 411–419.

    Google Scholar 

  95. M. Lahav, F. Laub, E. Gati, L. Leiscrowitz, and Z. Ludmer, A new method of enantiomeric purification via a topochemical photodimcrisation reaction. J. Am. Chem. Soc. 98, 1620–1622 (1976).

    Article  CAS  Google Scholar 

  96. T. Teitei, D. Wells, T. H. Spurling, and W. H. F. Sasse. Photodimers related to 2-methoxynaphthalene, Austral. J. Chem. 31, 85–96 (1978).

    Article  CAS  Google Scholar 

  97. R. Todesco, J. Gelan, H. Martens. J. Put, N. Boens, and F. C. de Schryver. Photochemistry of nonconjugated bichromophoric systems: Photocyclomerisation of di-(α-naphthylmethyl) ether. Tetrahedron Lett. 1978, 2815–2818.

    Google Scholar 

  98. N. Denms, A. R. Katritzky, and H. Wilde. Photochemically induced valence bond tautomerism and dimerisation of 3-oxido-l-phenylpyridinium. J. Chem. Soc. Perkin Trans. I 1976, 2338–2343.

    Google Scholar 

  99. H. Prinzbach, G. Sedelmeier, C. Krüger, R. Goddard, H-D Martin, and R. Gleiter. An unusual benzene/benzene through–space interaction, Angew. Chem. Int. Ed. 17, 271–272 (1978).

    Article  Google Scholar 

  100. I. Saito, M. Takami, and T. Matsuura. Oxidative cleavage of aromatic methoxy compounds with photo-excited aromatic nitro compounds. Bull. Chem. Soc. Jpn. 48, 2865–2871 (1975).

    Article  CAS  Google Scholar 

  101. H Morrison. Photochemistry of nonconjugated aryl-olefins. Org. Photochem. 4, 143 189 (1979); H. Morrison, Photochemistry of organic bichromophoric molecules, Acc. Chem. Res. 12, 383–389 (1979).

    Google Scholar 

  102. W. Ferree, J. Grutzner. and H. Morrison. Photochemistry of bichromophonc molecules. Intramolecular cycloaddition and cis–trans isomerisation of 6–phenyl–2–hexene in solution. J. Am. Chem. Soc. 93, 5502–5512 (1971).

    Article  CAS  Google Scholar 

  103. A. Gilbert and G. N. Taylor, Intramolecular photocycloaddition reactions of phenyl-vinyl bichromophoric systems, J. Chem. Soc. Perkin Trans. I 1980, 1761–1768.

    Google Scholar 

  104. P. A. Wender and J. J. Howbert. Synthetic studies on arene-olefin cycloadditions, J. Am. Chem. Soc. 103, 688–690 (1981); Tetrahedron Lett. 23, 3983–3986 (1982).

    Article  CAS  Google Scholar 

  105. A. S. Kushner. Photoisomerisation of the 1,4-naphlhoquinone-cyclopentadiene adduct. Tetrahedron Lett. 1971, 3275–3278.

    Google Scholar 

  106. W. M. Horspool. in: Photochemistry (D Bryce-Smith, ed.), Specialist Periodical Reports, Vols. 1-13, The Royal Society of Chemistry. London (1970–82).

    Google Scholar 

  107. J. J. Tufariello and D. W. Rowe, Synthesis of exo and endo tetracyclo[5.4.0.02,4.03,6]undeca-l(7),8,10–trien-5-ol and related derivatives, J. Org. Chem. 36, 2057–2065 (1971).

    Article  CAS  Google Scholar 

  108. H. E. Zimmennan and C. O. Bender. The di-π-methane rearrangement of the naphthobarrelenes, J. Am. Chem. Soc. 92, 4366–4376 (1970).

    Article  Google Scholar 

  109. M. Elian, M. Banciu, L. Stanescu, and E. Ciorancscu, Thermal and photochemical rearrangements of dibenzobullvalene and related dibenzo (CH)10 hydrocarbons, Ren. Roum. Chim. 21, 89–99 (1976).

    CAS  Google Scholar 

  110. H. Morrison, D. Giacherio, and F. J. Palensky, Photoinduced skeletal rearrangement of alkylindenes. J. Org. Chem. 47, 1051–1058 (1982).

    Article  CAS  Google Scholar 

  111. Y. Yamamoto, M. Irie, and K. Hayashi, Dimerisation of a methylstyrene via a photoexcited charge transfer complex, J. Chem. Soc. Perkin Trans. II 1979, 1517–1520.

    Google Scholar 

  112. R. Lapouyade, R. Koussini, and H. Bouas-Laurent, Primary and tertiary amines as catalysts of hydrogen transfer in the photocyclisation of 1.1-diarylethylenes. J. Am. Chem. Soc. 99, 7374–7376 (1977).

    Article  CAS  Google Scholar 

  113. W. Lippke, W. Ferree, and H. Morrison. Photochemistry of bichromophoric molecules. Internal photocycloaddition of 6-phenyl-2-hexyne. J. Am. Chem. Soc. 96, 2134–2137 (1974).

    Article  CAS  Google Scholar 

  114. L. M. Jackman, E. F. M. Stephenson, and H. C. Yick, The synthesis of cis l,2,3,4,4a,9a,hexahydro-l-methyl-6-methoxy-9-ozofluorene-l-carboxylic acid. Tetrahedron Lett. 1970, 3325–3328.

    Google Scholar 

  115. P. G. Sammes, Photoenolisation. Tetrahedron 32, 405–422 (1976).

    Article  CAS  Google Scholar 

  116. P. G. Sammes and T. W. Wallace. Photoinduced cyclisations of 3-arylchromones, J. Chem. Soc. Perkin Trans. I 1975, 1845–1849.

    Google Scholar 

  117. W. Oppolzer and K. Keller, Photoisomerisation of 2-[2-(N-ethoxy carbonyl-N-allylamino)ethyl]benzaldehyde. Angew. Chem. Int. Ed. 11, 728–730 (1972); See also G. Quinkert, U. Schwartz, H. Stark, W. D. Weber, F. Adam, H. Baier, G. Frank, and G. Duerner. Asymmetric total synthesis of 19-norsteroids via a photochemical key reaction: enantiomerically pure target compounds, Liebigs Ann. Chem. 11, 1999–2040 (1982).

    Google Scholar 

  118. M. Tada, H. Saiki, K. Miura, and H. Shinozaki. The photorcaction of benzyl 1-cycloalkenyl ketone in acidic or protic media. Bull. Chem. Soc. Jpn. 49, 1666–1670 (1976).

    Article  CAS  Google Scholar 

  119. M. Tada, H. Saika, H. Mizutani, and K Miura, The photoreaction of 1–cycloalkenyl phenethyl ketone. Bull. Chem. Soc. Jpn. 51, 343–344 (1978).

    Article  CAS  Google Scholar 

  120. A. G. Schultz, R. D. Lucci, W. Y. Fu, M. H. Berger. J. Erhardt. and W. K. Hagmann. Heteroatom directed photoarylation. Synthetic potential of the heteroatom oxygen. J. Am. Chem. Soc. 100, 2150–2162 (1978).

    Article  CAS  Google Scholar 

  121. A. G. Schultz and R. D. Lucci, Heteroatom directed photoarylation: synthesis of a tetracyclic morphine structural analogue, J. Chem. Soc. Chem. Commun. 1976, 925.

    Google Scholar 

  122. A. G. Schultz. W. Y. Fu, R. D. Lucci, B. G. Kurr, K. M. Lo, and M Boxer, Heteroatom directed photoarylation. Synthetic potential of the heteroatom sulphur, J. Am. Chem. Soc. 100, 2140–2149 (1978).

    Article  CAS  Google Scholar 

  123. T. Sasaki and K. Hayakawa, Photocyclisation of methyl 2-arylthioacetoacetates, a facile synthesis of benzothiophenes, Tetrahedron Lett. 1980, 1525–1526.

    Google Scholar 

  124. A. G. Schultz and V. Kane. A photochemical preparation of indoles, J. Chem. Ed. 56, 555–556 (1979).

    Article  CAS  Google Scholar 

  125. A. G. Schultz and W. K. Hagmann, Synthesis of 3-carboethoxyoxindoles, J. Org. Chem. 43, 4231–4233; Synthesis of indole-2-carboxylic esters. J. Org. Chem. 43, 3391–3393 (1978).

    Article  CAS  Google Scholar 

  126. I. Ninomiya, J. Yasui, and T. Kiguchi, Application of enamine photocyclisation to a total synthesis of (±)-cryptaustoline, Heterocycles 6, 1855–1860 (1977).

    Article  CAS  Google Scholar 

  127. A. G. Schultz and I. Ching Chiu, An approach to the synthesis of Aspidosperma alkaloids, J. Chem. Soc. Chem. Commun. 1978, 29.

    Google Scholar 

  128. T. Wolff and R. Waffenschmidt, Studies on the reaction mechanism of the photocyclisation of N-arylenamines. Dependence of quantum yields on back and side reactions, J. Am. Chem. Soc. 102, 6098–6102 (1980).

    Article  CAS  Google Scholar 

  129. G. R. Lenz, The photochemistry of enamides. Synthesis, 1978, 489–518.

    Google Scholar 

  130. I. Ninomiya, T. Kiguchi, S. Yamauchi, and T. Naito. Substituted effects in the photocyclisation of N-α,β-unsaturated acylanilides, J. Chem. Soc. Perkin Trans. I 1980, 197–202.

    Google Scholar 

  131. I. Ninomiya, S. Yaniauchi, T. Kiguchi, A. Shinohara. and T. Naito. Photocyclisation of α,β-unsaturated anilides, J. Chem. Soc. Perkin Trans. I 1974, 1747–1751.

    Google Scholar 

  132. Y. Kanaoka, S. Nakao, and Y Hatanaka. Stereochemistry of non-oxidative photocyclisation of indole-2-carboxanilides to an indolo(2,3-c] quinoline system. Heterocycles, 5, 261–266 (1976).

    Article  CAS  Google Scholar 

  133. Y. Kanaoka, K. Itoh, Y. Hatanaka, J. L. Flippen, I. L. Karle, and B. Witkop. Synthetic photochemistry with heterocyclic anilides. J. Org. Chem., 3001–3002 (1975).

    Google Scholar 

  134. Y. Kanaoka, K. Sannohe, Y. Hatanaka, K. Itoh, M Machida, and M. Tershima, Synthesis of thieno[2,3-c]-pyrrolo[2,3-c]-. and indolo[2.3-c] diazanaphthalene by photocyclisation of acylaminopyridines, Heterocycles 6, 29–32 (1977).

    Article  CAS  Google Scholar 

  135. J. E. Wolfe and M. A. Ogliaruso. in: The Chemistry of Acid Derivatives, Supplement B (S. Patai. ed), Wiley-Interscience. New York. Chap. 19, (1979)

    Google Scholar 

  136. J. D. Coyle, Photochemistry of carboxylic acid derivatives. Chem. Rev. 78, 97–123 (1978).

    Article  CAS  Google Scholar 

  137. I. Ninomiya, O. Yaniamoto, and T. Naito. Synthesis of the basic structures of corynoline and related alkaloids, J. Chem. Soc. Perkin Trans. I 1980, 203–207, 212–216.

    Article  Google Scholar 

  138. I. Ninomiya, T. Kiguchi, O Yamamoto, and T Naito. Substituent effects in the photocyclisation of A-benzoylenamines, J. Chem. Soc. Perkin Trans. I 1979, 1723–1728.

    Google Scholar 

  139. H. Ishii, E. Ueda, K Nakajima, T. Ishikawa, K. Harada, I. Ninomiya, T. Naito, and T. Kiguchi. Photocyclisation of cnamidcs. Chem. Pharm. Bull. 26, 864–873 (1978).

    CAS  Google Scholar 

  140. H. Iida, S. Aoyagi, Y. Yuasa, and C. Kibayashi, Synthesis of γ-lycoran and related compounds via photocyclisation of N-substituted β-enaminoketones. Heterocycles 6, 1747–1751 (1977).

    Article  CAS  Google Scholar 

  141. I. Ninomiya, O. Yamamoto, T. Kiguchi, T. Naito, and H. Ishii, Enamide photocyclisation in the synthesis of benzo[c] phenanthridine alkaloids, Heterocycles 6, 1730–1734 (1977).

    Article  CAS  Google Scholar 

  142. H. P. Soetens and U. K. Pandit. Photocyclisation of 4-substituted isoquinolinonc. An approach to the synthesis of phenanthridine alkaloids, Heterocycles. 8, 181–186 (1977).

    Google Scholar 

  143. M. Sainsbury and N. L. Uttley, Chemical and photochemical cychsations of 1-alkylidene-l,2.3,4-tetrahydro-2-nicotinoyl and isonicotinoyl-β-carbolines. J. Chem. Soc. Perkin Trans. I 1977, 2109–2115.

    Google Scholar 

  144. G. J Fonken, Photochemical formation of polynuclear aromatic compounds from diaryl polyenes. Chem. Ind. 1962, 1327.

    Google Scholar 

  145. R. Srinivasan, V. Y. Meritt, J. N. C. Hsu. P H. G Op Het Veld, and W. H. Laarhoven. Photocyclisations of α-(l-cyclohexenyl) cinnamic esters. J. Org. Chem. 43, 980–985

    Google Scholar 

  146. I. Saito, K. Shomozono, S. Miyazaki, T. Matsuura, K. Fukujama, and Y Katsube, Photoaddition of 6-cyano-l,3-dimethyl uracil with acetylenic compounds, Tetrahedron Lett. 1980, 2317–2320.

    Google Scholar 

  147. F. Fournier, S. Altenburger-Combrisson, N. K Cuong, and J. J. Basselier. Rearrangements photochimiques d’ethenylfurannes, Tetrahedron 35, 2639–2644 (1979).

    Article  CAS  Google Scholar 

  148. T. Wismontski-Knittel, M. Kaganowitch, G. Seger, and E. Fischer, The reversible photochemistry of 1,2-di-(2-naphthyl)cyclopentene, Rec. Trav. Chim. Pays-Bas 98, 114–117 (1979).

    Article  CAS  Google Scholar 

  149. H. G. Heller and M. Szewczyk, Photoreactions of photochromic (α-phenyl ethylidene) (substituted methylene) succinic anhydride, J. Chem. Soc. Perkin Trans. I 1974, 1487–1492. O. Crescente, H. G. Heller, and S. Oliver. Thermal and photochemical reactions of (E.F.)-bis(benzylidene) succinic anhydride. J. Chem. Soc. Perkin Trans I 1979, 150–153.

    Google Scholar 

  150. P. J. Darcy, R. J. Hart, and H. G. Heller. Photochromic systems involving (Z)-l-methylpropylidene (diphenylmethylene) succinic and (E)-3,5-dimethoxybenzylidene (alkyl substituted methylene) succinic anhydride, J. Chem. Soc. Perkin Trans. I 1978, 571–576.

    Google Scholar 

  151. H. D. Ilge and R. Paetzold. On photochromism of fulgides. J. Signalaufzeichnungsmaterialen, 5, 5–10 (1977).

    CAS  Google Scholar 

  152. T. Momose, K. Kanai, T. Nakamura, and Y. Kuni, Regiospecificity in the photocyclisation of 2,3-dibenzylidenebutyrolactones, Chem. Pharm. Bull. 25, 2755–2760 (1977).

    CAS  Google Scholar 

  153. T. Momose, T. Nakamura, and J. Kanai. Photochemical rearrangement of β-apolignans, Chem. Pharm. Bull. 26, 1592–1597 (1978).

    CAS  Google Scholar 

  154. T. Momosc, K. Kanai, and K. Hayashi, Synthetic studies on lignans and related compounds. Chem. Pharm. Bull. 26, 3195–3198 (1978).

    Google Scholar 

  155. A. H. A. Tinnemans and W. H. Laarhoven, A novel photocyclisation starting from 1,4-diarylbutenynes. Tetrahedron Lett. 1973, 817–820.

    Google Scholar 

  156. A. H. A. Tinnemans and W. H. Laarhove, Photocyclisation of l,4-diarylbut-1-en-3-ynes, J. Chem. Soc. Perkin Trans. II 1976, 1111–1115, 1115–1120.

    Article  Google Scholar 

  157. R. J. F. M. Van Arendonk and W. H. Laarhoven, The formation of a cyclopropanone in the photocyclisation of 1-(9-phenanthryl)-4-phenylbut-1-en-3-yne. Tetrahedron Lett. 1977, 2629–2630.

    Google Scholar 

  158. F. Toda and Y. Todo, The photocyclisation of 3,3’-diphenyl-2,2’-bi-1H-indene-1,’-dione, Bull. Chem. Soc. Jpn. 3000–3001 (1977).

    Google Scholar 

  159. M. Maienthal, W. R. Bensons, E. B. Sheinin, T. D. Doyle, and N. Filipescu, cis-4,4’-Stilbenediols. Synthesis from dienestrol. structure and photocyclisation to dihydrophenanthrenes. J. Org. Chem. 43, 972–975 (1978).

    Article  CAS  Google Scholar 

  160. J. Bendig, M. Bayermann, and D. Kreysig, Photodehydrocyclisations of stilbenes and stilbene-like compounds in the presence of π-acceptors, Tetrahedron Lett. 1977, 3659–3660.

    Google Scholar 

  161. A. Buquet, A. Couture, and A. Lablache-Combier. Photocyclisation reactions in primary amines. Convenient synthesis of 1,4-dihydrophenanthrene, J. Org. Chem. 44, 2300–2303 1979 ).

    Article  CAS  Google Scholar 

  162. E. V. Blackburn, C. E. Loader, and C. J. Timmons, The ultraviolet, proton magnetic resonance, and mass spectra, and photocyclisation of some styrylnaphthalenes to some benzo[c]phenanthrenes and chrysenes, J. Chem. Soc. 1970, 163–172.

    Google Scholar 

  163. R. G. F. Giles and M. V. Sargent. Photocyclisation of o-methoxystilbenes to phenanthrenes with loss of the methoxy group. J. Chem. Soc. Chem. Commun. 1974, 215–216.

    Google Scholar 

  164. B. I. Rosen and W. P. Weber. Synthesis of 7,12-Benz [a] anthraquinones via Diels Alder reaction of 1.4-phenanthraquinones, J. Org. Chem. 42, 3463–3465 (1977).

    Article  CAS  Google Scholar 

  165. Y. Kanaoka and K. Itoh. Photocyclisation of benzanilides to phenanthridone with elimination of the o-methoxy group, J. Chem. Soc. Chem. Commun. 1973, 647–648.

    Google Scholar 

  166. J. A. Elix, D. P. H. Murphy, and M. V. Sargent. Photocyclisation of 2-methoxyphenyl phenyl ethers, Synthetic Commun. 2, 427–430 (1972).

    Article  CAS  Google Scholar 

  167. R. Srinivasan and J. N. C. Hsu, Photoisomerisation of certain stilbenes to 9,10-dihydrophenanthrenes, J. Am. Chem. Soc. 93, 2816–2817 (1971).

    Article  CAS  Google Scholar 

  168. T. Wismontski-Knittel, M. A. Muszkat, and E. Fischer, Photoinduced reactions of α,β-dicyanostilbene, Mol. Photochem. 9, 217–225 (1979).

    CAS  Google Scholar 

  169. C. J. Cardin, D. J. Cardin, J. M. Kelly, D. J. H. L. Kirwan, R. J. Norton, and A. Roy. Preparation and properties of some alkenyl-tin compounds, Proc. R. Ir. Acad. Sec. B 77, 365–369 (1977).

    Google Scholar 

  170. O. Tsuge, K. Oe, and H. Inoue, Photocyclisation and photooxygenation of 1,3,4,5-tetraarylimidazolin-2-ones. Heterocycles 12, 217–225 (1979).

    Article  CAS  Google Scholar 

  171. J. Glinka. Oxidative photocyclisation of 2-benzyl-3.4-iphenylquinoline to 9–benzyldibenzo [i,k]phenanthridine, Zesz. Sauk. Politech. Slask. Chem. 1978, 75–79, [Chem. Abs. 92, 110814 (1980)].

    Google Scholar 

  172. I. Lantos, A new photochemically based synthesis of phenanthrene-9,10-quinones, Tetrahedron Lett. 1978, 2761–2762.

    Google Scholar 

  173. D. L. Nagel, R Kupper, K Antonson, and L. Wallcave, Synthesis of alkyl-substituted benzo [c] phenanthrenes and chrysenes by photocyclisation. J. Org. Chem. 42, 3626–3628 (1977).

    Article  CAS  Google Scholar 

  174. P. H. Gore and F. S. Kamonah, Photochemical synthesis of some mono-substituted chrysenes. Synthesis 1978, 773–775.

    Google Scholar 

  175. C. E. Browne, T. K. Dobbs, S. S. Hecht, and E. J. Eisenbrown, Stereochemical assignment of (E)- and (Z)-2-(l-naphthyl)-1-phenylpropene and their photocyclisation to 5-methylchrysene, J. Org. Chem. 43, 1656–1660 (1978).

    Article  CAS  Google Scholar 

  176. T. S. Skorokhodova, V. I. Luk’Yanov, and E. B. Merkusheve. Photochemical synthesis of 5,6-benzopicene, Izv. Akad. Nauk. SSR Khim. 1979, 1918, [Chem. Ads. 92, 6305 (1980)].

    Google Scholar 

  177. A. Padwa, C. Doubleday, and A. Mazzu, Photocyclisation reactions of substituted 2,2’-divinylbiphenyl derivatives. J. Org. Chem. 42, 3271–3279 (1977).

    Article  CAS  Google Scholar 

  178. K. H. Grellmann, P. Hentzchel, T Wismontski-Knittel, and E. Fischer. The photophysics and photochemistry of pentahelicene, J. Photochem. 11, 197–213 (1979)

    Article  CAS  Google Scholar 

  179. R. H. Martin, C. Eyndels, and N. Defay, Double hdicenes. Tetrahedron 30, 3339–3342 (1974); W. H. Laarhoven, T. J. H. M. Cuppen, and R J. F. Nivard. Photodehydrocy-clisations of stilbene-like compounds, Tetrahedron 30, 3343–3347 (1974).

    Article  Google Scholar 

  180. W. H. Laarhoven and T. J. H. M. Cuppen, Chiral solvent induced asymmetric synthesis. Photosynthesis of optically enriched hexahelicenes, J. Chem. Soc. Perkin Trans. II 1978, 315–323.

    Google Scholar 

  181. R. H. Martin and V. Libert, The use of resolved hcxahelicene-2-carboxylic acid as a common precursor for the photochcmical synthesis of optically pure octahelicenes, J. Chem. Res. 1980, 130–131.

    Google Scholar 

  182. K. Yamamoto. K. Fukiwara. and M. Maeda. Mechanically directed absolute asymmetric synthesis of helicenes in a twisted nematic mesophase, J. Chem. Soc. Chem. Commun. 1979, 1086–1087.

    Google Scholar 

  183. P. L. Kumler and R. A Dybas, Effect of structural features on the photocyclisation of 2-stilbazole derivatives, J. Org. Chem. 35, 3825–3831 (1970).

    Article  CAS  Google Scholar 

  184. G. Karminski-Zamola and K. Jakopcic, Synthesis of naphtho(2,l-b) furancarboxylic acids by oxidative photochcmical cyclisation of substituted furylacrylic acids, Bull. Sci. Conseil Acad. Dir. Arts RSF. Yougaslavie. Sec. A. 21, 134–135 (1976).

    CAS  Google Scholar 

  185. A. Shaflcc and A. Rashidbaigi. Photochemical synthesis of [I] benzothieno-[3,2-h] isoquinoline. J. Heterocyclic Chem. 13, 141–144 (1976).

    Article  Google Scholar 

  186. A. Mitschker, U. Brandl, and T. Kauffmann, Neue ringsystcme durch photocyclisierung heterocyclischer triarene. Tetrahedron Lett. 1974, 2343–2346.

    Google Scholar 

  187. A. V. Eltsov, O. P. Studzinskii, and N. V. Ogoltsova, Photochcmical dehydrocyclisation of acctophenone anils, Zh. Org. Khim. 6, 405–406(1970); M. P. Cava and R. H. Schlessinger. The synthesis of a phenanthridene from an aromatic Schiff base by a photo-oxidative closure. Tetrahedron Lett. 1964, 2109–2111.

    Google Scholar 

  188. T. Onaka, Y. Kanda, and M. Natsume. An application of the photocyclisation reaction of Schiff bases to the synthesis of a phenanthridine alkaloid. Tetrahedron Lett. 1974, 1179–1180.

    Google Scholar 

  189. R. Salsman and G. van Binst, A novel route to the tribenzo [a,ch] quinolirinc system by electrophilic and photolytic cyclisation of immonium salts, Heterocycles 4, 1007–1011 (1976).

    Article  Google Scholar 

  190. R. E. Doolittle and C. K. Bradsher. Photochemical methods in the synthesis of heterocyclic compounds, J. Org. Chem. 31, 2616–2618 (1966).

    Article  CAS  Google Scholar 

  191. C. P. Joshua and V. N. R. Pillai. Photochemical cyclodehydrogenation of Lewis acid-conjugates of azobenzenes. Tetrahedron 30, 3333–3337 (1974).

    Article  CAS  Google Scholar 

  192. J. W. Barton and R. B. Walker. Synthesis of monoazabiphenylenes. Tetrahedron Lett. 1975, 569–572.

    Google Scholar 

  193. H. H. Perkampus and B. Behjati, Preparation of a diazophenanthrene by the photocyclisation of benzylidenaminopyridine and pyridinalanaline. J. Heterocyclic Chem. 11, 511 — 514 (1974).

    Article  CAS  Google Scholar 

  194. V. N. R Pillai and E. Purushothaman. Photocyclisation of 2-phenylazopyndine formation of 4-pyrido[c]cinnoline, Current Sci. 46, 381–382 (1977).

    CAS  Google Scholar 

  195. A. H. A. Tinnemans and W. H. Laarhoven, 4-Phenanthrene and 3-iodo-4-phenylphenanthrene, Org. Photochem. Syn. 2, 93–95 (1976).

    CAS  Google Scholar 

  196. J. A. Elix and D. P. Murphy. The photocyclisation of 2-methoxyphenyl phenyl ethers, Austral. J. Chem. 28, 1559–1582 (1975).

    CAS  Google Scholar 

  197. V. R. Tymyanskii, M. I. Knyazhanskii, Yu. P. Andreichikov, G. E. Trukhan, and G. N. Dorofeenko, Photocyclisation of N-phenylpyridinium perchlorates. Zh. Org. Khim. 12, 1126–1227 (1976). [Chem. Abs. 85, 10 2252f ].

    Google Scholar 

  198. J. Glinka. Oxidational photocyclisation of 3.4-diphenylquinolone to dibenzo [i,k]phenanthridine, Rocz. Chem. 51, 577–582 (1977).

    CAS  Google Scholar 

  199. C. Mortelmans and G. van Binst, Synthesis of 9.10-dihydro-8bH-quino (1,2-f) phenanthridine and 6-phenyl-4,5,6,7-tetrahydropyrido[3,2,l-j,k) carbazole derivatives. Tetrahedron 34, 363–369 (1978).

    Article  CAS  Google Scholar 

  200. C-I. Lin, P. Singh, M. Maddox, and E. F. Ullman, Photochemical preparation of a [3.1] metacyclophane and [3.2] metacyclophane through internal charge-transfer sensitisation. J. Am. Chem. Soc. 102, 3261–3262 (1980).

    Article  CAS  Google Scholar 

  201. J. E. Rockley and L. A. Summers. Synthesis of thieno [3.2-c: 4,5-c’] pyridine by photolysis of 4,4’-thiodipyridine, Chem. Ind. 1979, 666–667.

    Google Scholar 

  202. H. Iida, T. Takarai, and C. Kibayashi, Facile syntheses of hexahydroapocrysopine via intramolecular photoarylation of β-enamino ketones. J. Org. Chem. 43, 975–979 (1978).

    Article  CAS  Google Scholar 

  203. S. Lalitha, S. Rajeswari, B. R. Pai, and H. Suguna. Synthesis of 3-hydroxy- and 8-hydroxyphenanthridone by a photochemical method, Indian J. Chem. B15, 180–182 (1977).

    Google Scholar 

  204. See for example H. Suguna and B. R. Pai. Photolytic syntheses of dl-anolobine and dl-9-hydroxy-2,3-methylenedioxyberbine, Indian J. Chem. B15, 416–418 (1977).

    Google Scholar 

  205. S. Rajcswari, H. Suguna, and B. R. Pai. Photolytic syntheses of dl-laurolitsine and dl-aequaline, Indian J. Chem. B15, 592–594 (1977).

    Google Scholar 

  206. S. Prabhakar, A. M. Lobo, and M. R. Tavares, Boron complexes as control synthons in photocyclisations: An improved phcnanthndine synthesis, J. Chem. Soc. Chem. Commun. 1978, 884–885.

    Google Scholar 

  207. T. Trifonov and A. Orakhavats. Application of organic photochemistry in the synthesis of (I) glaucine. Izv. Khim. 11, 297–304 (1978). [Chem, Abs. 92, 164–129 (1980)].

    Google Scholar 

  208. D. A. Whiting and A. F. Wood, Cyclisation of 1,7-diarylheptanoids through oxidative, reductive and photochemical radical processes. Tetrahedron lett. 1978, 2335–2338.

    Google Scholar 

  209. R. Dessaker and J. P. Paris, Photochromism, Adv. Photochem. 1, 275–321 (1963); J. D. Margerum and L. J. Miller, in: Photochromism (G. H. Brown, ed.), p 580, Wiley Interscience. New York (1971).

    Google Scholar 

  210. P. de Mayo and S. T. Reid. Photochemical rearrangements and related transformations, Q. Rev. Chem. Soc. 15, 393–417 (1961).

    Article  Google Scholar 

  211. D, Döpp. Reactions of aromatic nitro compounds via excited triplet states. Topp. Curr. Chem. 55, 49–85 (1975).

    Article  Google Scholar 

  212. C. C. Leznoff and R. J. Hayward, Photocyclisation reactions of aryl polyenes, Canad. J. Chem. 49, 3596–3601 (1971).

    Article  CAS  Google Scholar 

  213. U. Koch-Pomeranz, H. Schmid, and H. J. Hanson. Photochemische cyclisierung von o-,m-, and p-allylanisolen und allylanilinen, Helv. Chim. Acta. 60, 768–797 (1977).

    Article  CAS  Google Scholar 

  214. K. Mutai, S. Kanno, and K. Kobayash, Photocyclisation in 3-[w-(anilino)alkoxy]-nitro- benzenes, Chem. Lett. 1978, 931–932.

    Google Scholar 

  215. J. P. Ferris and F. R. Antonucci. Photochemistry of ortho substituted benzene derivatives and related heterocycles. J. Am. Chem. Soc. 96, 2010–2014 (1974).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Reading, Whiteknights, Reading, Berkshire, RG6 2AD, England

    Andrew Gilbert

Authors
  1. Andrew Gilbert
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Chemistry, The University of Dundee, DD1 4HN, Dundee, UK

    William M. Horspool

Rights and permissions

Reprints and permissions

Copyright information

© 1984 Plenum Press, New York

About this chapter

Cite this chapter

Gilbert, A. (1984). Photoaddition and Photocyclization Processes of Aromatic Compounds. In: Horspool, W.M. (eds) Synthetic Organic Photochemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-2681-6_1

Download citation

  • DOI: https://doi.org/10.1007/978-1-4613-2681-6_1

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4612-9668-3

  • Online ISBN: 978-1-4613-2681-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation