Advertisement

Photoaddition and Photocyclization Processes of Aromatic Compounds

  • Andrew Gilbert
Chapter

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)

Keywords

Aromatic Compound Maleic Anhydride Succinic Anhydride Dimethyl Acetylene Dicarboxylate Ethyl Vinyl Ether 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    J. M. Blair and D. Bryce-Smith, The photoisomerisation of benzene to fulvene, Proc. Chem. Soc. 1957, 287–288.Google Scholar
  2. 2.
    H. J. F. Angus and D. Bryce-Smith. Addition of maleic anhydride to benzene, Proc. Chem. Soc. 1959, 326–327.Google Scholar
  3. 3.
    D. Bryce-Smith and A. Gilbert, The organic photochemistry of benzene I. Tetrahedron 32, 1309–1327 (1976).CrossRefGoogle Scholar
  4. 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. 5.
    G. Kaupp. Photochemical rearrangements and fragmentations of benzene derivatives and annelated arenes. Angew. Chem. Int. Ed. 19, 243–275 (1980).CrossRefGoogle Scholar
  6. 6.
    See for example E. Havinga and H. Cornelisse, Aromatic photosubstitution reactions, Pure Appl. Chem. 47, 1–10 (1976).CrossRefGoogle Scholar
  7. 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. 8.
    D. Bryce-Smith and A. Gilbert, The organic photochemistry of benzene II. Tetrahedron 33, 2459–2489 (1977).CrossRefGoogle Scholar
  9. 9.
    A. Gilbert, The inter- and intramolecular photocycloaddition of ethylenes to aromatic compounds. Pure Appl. Chem. 52, 2669–2682 (1980).CrossRefGoogle Scholar
  10. 10.
    T. Wagner-Jauregg. Thermische und photochemische additionen von dienophilen an arene und deren vinyloge und heteroanaloge. Synthesis 1980. 165–214.Google Scholar
  11. 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. 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).CrossRefGoogle Scholar
  13. 13.
    G. Kaupp, Photo-Diels-Alder Reaktionen mit anthracen, Justus Liebig’s Ann. Chem. 2, 254–275 (1977).CrossRefGoogle Scholar
  14. 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. 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, 869–876Google Scholar
  16. 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. 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. 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. 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. 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. 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).CrossRefGoogle Scholar
  22. 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. 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).CrossRefGoogle Scholar
  24. 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. 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. 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. 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).CrossRefGoogle Scholar
  28. 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. 29.
    D. Bryce-Smith, Photoaddition and photoisomerisation reactions of the benzene ring. Pure Appl. Chem. 16. 47–63 (1968).CrossRefGoogle Scholar
  30. 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. 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. 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. 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. 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. 35.
    M. P. Stevens. Photopolymerisation and crosslinking by the benzene-bimaleimide photoaddition reaction, Am. Chem. Soc. Symp. Ser. 25, 64–75 (1976).Google Scholar
  36. 36.
    D. Bryce-Smith. Photoaddition to the benzene ring. Pure Appl. Chem. 34, 193–212 (1973).CrossRefGoogle Scholar
  37. 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. 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. 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. 40.
    T. S. Cantrell. Photochemical cycloadditions of benzonitrile to alkenes. Factors controlling the site of addition, J. Am. Chem. Soc. 42, 4238–4245 (1977).Google Scholar
  41. 41.
    J. L. Charlton and P. de Mayo. The Photocycloaddition of nitrobenzene to alkenes, Can. J. Chem. 46, 1041–1042 (1968).CrossRefGoogle Scholar
  42. 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. 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. 43.
    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. 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).CrossRefGoogle Scholar
  46. 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).CrossRefGoogle Scholar
  47. 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. 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).CrossRefGoogle Scholar
  49. 49.
    R. A. Caldwell and D. Creed. Exiplex intermediates in 2 + 2 photocycloaddilions. Acc. Chem. Res. 13, 45–50 (1980).CrossRefGoogle Scholar
  50. 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).CrossRefGoogle Scholar
  51. 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).CrossRefGoogle Scholar
  52. 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. 53.
    I. Saito, K. Kanehira, K. Shimozono, and T. Matsuura, Photoaddition of 2-cyanopyridine to olefins. Tetrahedron Lett. 1980, 2737–2740.Google Scholar
  54. 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 )CrossRefGoogle Scholar
  55. 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. 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. 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. 58.
    D Bryce-Smith, A. Gilbert, and J. Grzonka, Photoaddition of acetylenes to benzene. Chem. Commun. 1970, 498–499.Google Scholar
  59. 59.
    J. Grzonka, The Photoaddition of acetylenes to benzene and benzene derivatives, Ph.D thesis. Reading (1973).Google Scholar
  60. 60.
    B. Sket and M. Zupan, 2 + 2 Photoaddition of acetylenes to hexafluorobenzene. J. Am. Chem. Soc. 99, 3504–3505 (1977).CrossRefGoogle Scholar
  61. 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. 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).CrossRefGoogle Scholar
  63. 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).CrossRefGoogle Scholar
  64. 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. 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).CrossRefGoogle Scholar
  66. 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).CrossRefGoogle Scholar
  67. 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.CrossRefGoogle Scholar
  68. 68.
    H. P. Locffler. Synthese von bicyclo[4.2.2]deca-2.4.7.9-tetraen. Tetrahedron Lett. 1974, 787–788.Google Scholar
  69. 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).CrossRefGoogle Scholar
  70. 70.
    N. C. Yang and J. Libman. Photochemical additions of 1.3-dienes to benzene. Tetrahedron Lett. 1973, 1409–1412.Google Scholar
  71. 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. 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. 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).CrossRefGoogle Scholar
  74. 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. 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).CrossRefGoogle Scholar
  76. 76.
    See for example The Exiplex (M. Gordon and W. R. Ware, eds.), Academic Press. New York (1975). and references therein.Google Scholar
  77. 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. 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. 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. 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. 81.
    J. A. Barltrop, The photoreduction of aromatic systems. Pure Appl. Chem. 33, 179–195 (1973).CrossRefGoogle Scholar
  82. 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. 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).CrossRefGoogle Scholar
  84. 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. 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. 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. 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).CrossRefGoogle Scholar
  89. 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).Google Scholar
  90. 90.
    S. Futamura, H. Ohta, and Y. Kamiya, Photoesterification of phcnanthridinc in carboxylic acid. Tetrahedron Lett. 1979, 4299–4302.Google Scholar
  91. 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. 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).CrossRefGoogle Scholar
  93. 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).CrossRefGoogle Scholar
  94. 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. 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).CrossRefGoogle Scholar
  96. 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).CrossRefGoogle Scholar
  97. 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. 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. 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).CrossRefGoogle Scholar
  100. 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).CrossRefGoogle Scholar
  101. 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. 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).CrossRefGoogle Scholar
  103. 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. 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).CrossRefGoogle Scholar
  105. 105.
    A. S. Kushner. Photoisomerisation of the 1,4-naphlhoquinone-cyclopentadiene adduct. Tetrahedron Lett. 1971, 3275–3278.Google Scholar
  106. 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. 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).CrossRefGoogle Scholar
  108. 108.
    H. E. Zimmennan and C. O. Bender. The di-π-methane rearrangement of the naphthobarrelenes, J. Am. Chem. Soc. 92, 4366–4376 (1970).CrossRefGoogle Scholar
  109. 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).Google Scholar
  110. 110.
    H. Morrison, D. Giacherio, and F. J. Palensky, Photoinduced skeletal rearrangement of alkylindenes. J. Org. Chem. 47, 1051–1058 (1982).CrossRefGoogle Scholar
  111. 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. 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).CrossRefGoogle Scholar
  113. 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).CrossRefGoogle Scholar
  114. 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. 115.
    P. G. Sammes, Photoenolisation. Tetrahedron 32, 405–422 (1976).CrossRefGoogle Scholar
  116. 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. 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. 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).CrossRefGoogle Scholar
  119. 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).CrossRefGoogle Scholar
  120. 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).CrossRefGoogle Scholar
  121. 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. 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).CrossRefGoogle Scholar
  123. 123.
    T. Sasaki and K. Hayakawa, Photocyclisation of methyl 2-arylthioacetoacetates, a facile synthesis of benzothiophenes, Tetrahedron Lett. 1980, 1525–1526.Google Scholar
  124. 124.
    A. G. Schultz and V. Kane. A photochemical preparation of indoles, J. Chem. Ed. 56, 555–556 (1979).CrossRefGoogle Scholar
  125. 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).CrossRefGoogle Scholar
  126. 126.
    I. Ninomiya, J. Yasui, and T. Kiguchi, Application of enamine photocyclisation to a total synthesis of (±)-cryptaustoline, Heterocycles 6, 1855–1860 (1977).CrossRefGoogle Scholar
  127. 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. 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).CrossRefGoogle Scholar
  129. 129.
    G. R. Lenz, The photochemistry of enamides. Synthesis, 1978, 489–518.Google Scholar
  130. 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. 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. 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).CrossRefGoogle Scholar
  133. 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. 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).CrossRefGoogle Scholar
  135. 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. 136.
    J. D. Coyle, Photochemistry of carboxylic acid derivatives. Chem. Rev. 78, 97–123 (1978).CrossRefGoogle Scholar
  137. 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.CrossRefGoogle Scholar
  138. 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. 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).Google Scholar
  140. 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).CrossRefGoogle Scholar
  141. 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).CrossRefGoogle Scholar
  142. 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. 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. 144.
    G. J Fonken, Photochemical formation of polynuclear aromatic compounds from diaryl polyenes. Chem. Ind. 1962, 1327.Google Scholar
  145. 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, 980–985Google Scholar
  146. 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. 147.
    F. Fournier, S. Altenburger-Combrisson, N. K Cuong, and J. J. Basselier. Rearrangements photochimiques d’ethenylfurannes, Tetrahedron 35, 2639–2644 (1979).CrossRefGoogle Scholar
  148. 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).CrossRefGoogle Scholar
  149. 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. 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. 151.
    H. D. Ilge and R. Paetzold. On photochromism of fulgides. J. Signalaufzeichnungsmaterialen, 5, 5–10 (1977).Google Scholar
  152. 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).Google Scholar
  153. 153.
    T. Momose, T. Nakamura, and J. Kanai. Photochemical rearrangement of β-apolignans, Chem. Pharm. Bull. 26, 1592–1597 (1978).Google Scholar
  154. 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. 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. 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.CrossRefGoogle Scholar
  157. 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. 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. 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).CrossRefGoogle Scholar
  160. 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. 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 ).CrossRefGoogle Scholar
  162. 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. 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. 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).CrossRefGoogle Scholar
  165. 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. 166.
    J. A. Elix, D. P. H. Murphy, and M. V. Sargent. Photocyclisation of 2-methoxyphenyl phenyl ethers, Synthetic Commun. 2, 427–430 (1972).CrossRefGoogle Scholar
  167. 167.
    R. Srinivasan and J. N. C. Hsu, Photoisomerisation of certain stilbenes to 9,10-dihydrophenanthrenes, J. Am. Chem. Soc. 93, 2816–2817 (1971).CrossRefGoogle Scholar
  168. 168.
    T. Wismontski-Knittel, M. A. Muszkat, and E. Fischer, Photoinduced reactions of α,β-dicyanostilbene, Mol. Photochem. 9, 217–225 (1979).Google Scholar
  169. 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. 170.
    O. Tsuge, K. Oe, and H. Inoue, Photocyclisation and photooxygenation of 1,3,4,5-tetraarylimidazolin-2-ones. Heterocycles 12, 217–225 (1979).CrossRefGoogle Scholar
  171. 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. 172.
    I. Lantos, A new photochemically based synthesis of phenanthrene-9,10-quinones, Tetrahedron Lett. 1978, 2761–2762.Google Scholar
  173. 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).CrossRefGoogle Scholar
  174. 174.
    P. H. Gore and F. S. Kamonah, Photochemical synthesis of some mono-substituted chrysenes. Synthesis 1978, 773–775.Google Scholar
  175. 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).CrossRefGoogle Scholar
  176. 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. 177.
    A. Padwa, C. Doubleday, and A. Mazzu, Photocyclisation reactions of substituted 2,2’-divinylbiphenyl derivatives. J. Org. Chem. 42, 3271–3279 (1977).CrossRefGoogle Scholar
  178. 178.
    K. H. Grellmann, P. Hentzchel, T Wismontski-Knittel, and E. Fischer. The photophysics and photochemistry of pentahelicene, J. Photochem. 11, 197–213 (1979)CrossRefGoogle Scholar
  179. 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).CrossRefGoogle Scholar
  180. 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. 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. 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. 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).CrossRefGoogle Scholar
  184. 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).Google Scholar
  185. 185.
    A. Shaflcc and A. Rashidbaigi. Photochemical synthesis of [I] benzothieno-[3,2-h] isoquinoline. J. Heterocyclic Chem. 13, 141–144 (1976).CrossRefGoogle Scholar
  186. 186.
    A. Mitschker, U. Brandl, and T. Kauffmann, Neue ringsystcme durch photocyclisierung heterocyclischer triarene. Tetrahedron Lett. 1974, 2343–2346.Google Scholar
  187. 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. 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. 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).CrossRefGoogle Scholar
  190. 190.
    R. E. Doolittle and C. K. Bradsher. Photochemical methods in the synthesis of heterocyclic compounds, J. Org. Chem. 31, 2616–2618 (1966).CrossRefGoogle Scholar
  191. 191.
    C. P. Joshua and V. N. R. Pillai. Photochemical cyclodehydrogenation of Lewis acid-conjugates of azobenzenes. Tetrahedron 30, 3333–3337 (1974).CrossRefGoogle Scholar
  192. 192.
    J. W. Barton and R. B. Walker. Synthesis of monoazabiphenylenes. Tetrahedron Lett. 1975, 569–572.Google Scholar
  193. 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).CrossRefGoogle Scholar
  194. 194.
    V. N. R Pillai and E. Purushothaman. Photocyclisation of 2-phenylazopyndine formation of 4-pyrido[c]cinnoline, Current Sci. 46, 381–382 (1977).Google Scholar
  195. 195.
    A. H. A. Tinnemans and W. H. Laarhoven, 4-Phenanthrene and 3-iodo-4-phenylphenanthrene, Org. Photochem. Syn. 2, 93–95 (1976).Google Scholar
  196. 196.
    J. A. Elix and D. P. Murphy. The photocyclisation of 2-methoxyphenyl phenyl ethers, Austral. J. Chem. 28, 1559–1582 (1975).Google Scholar
  197. 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. 198.
    J. Glinka. Oxidational photocyclisation of 3.4-diphenylquinolone to dibenzo [i,k]phenanthridine, Rocz. Chem. 51, 577–582 (1977).Google Scholar
  199. 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).CrossRefGoogle Scholar
  200. 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).CrossRefGoogle Scholar
  201. 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. 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).CrossRefGoogle Scholar
  203. 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. 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. 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. 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. 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. 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. 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. 210.
    P. de Mayo and S. T. Reid. Photochemical rearrangements and related transformations, Q. Rev. Chem. Soc. 15, 393–417 (1961).CrossRefGoogle Scholar
  211. 211.
    D, Döpp. Reactions of aromatic nitro compounds via excited triplet states. Topp. Curr. Chem. 55, 49–85 (1975).CrossRefGoogle Scholar
  212. 212.
    C. C. Leznoff and R. J. Hayward, Photocyclisation reactions of aryl polyenes, Canad. J. Chem. 49, 3596–3601 (1971).CrossRefGoogle Scholar
  213. 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).CrossRefGoogle Scholar
  214. 214.
    K. Mutai, S. Kanno, and K. Kobayash, Photocyclisation in 3-[w-(anilino)alkoxy]-nitro- benzenes, Chem. Lett. 1978, 931–932.Google Scholar
  215. 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).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1984

Authors and Affiliations

  • Andrew Gilbert
    • 1
  1. 1.Department of ChemistryUniversity of ReadingWhiteknights, Reading, BerkshireEngland

Personalised recommendations