Photoreactions of some monoaryl- and diaryl-p-benzoquinones in solution. Dependence of dimerizations, cyclizations and rearrangements on the substituents and solvents

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 103, Issue 1-2, 1997, Pages 75-83

  Hageman, Hendrik J ^a,c   Verhoeven, Jan W ^b  

^a AKZO NOBEL CENTRAL RESEARCH   (Netherlands)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

^c UNIVERSITY OF KENT   (United Kingdom)

Author keywords

Aryl p benzoquinones; Photoreactions; Substituent and solvent effects

Indexed keywords

EID: 0031565217     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1010-6030(96)04527-3     Document Type: Article

References (38)

1. [1] H.J. Hageman, in E. Müller (ed.), Methoden der Organischen Chemie, Houben-Weyl, G. Thieme Verlag, Stuttgart, 1975, Band IV/5b, Photochemie Teil II, p. 941. J.M. Bruce, in S. Patai (ed.), The Chemistry of Quinonoid Compounds, Wiley, 1974, Part 1. Chapter 9, p. 465.
2. [1] H.J. Hageman, in E. Müller (ed.), Methoden der Organischen Chemie, Houben-Weyl, G. Thieme Verlag, Stuttgart, 1975, Band IV/5b, Photochemie Teil II, p. 941. J.M. Bruce, in S. Patai (ed.), The Chemistry of Quinonoid Compounds, Wiley, 1974, Part 1. Chapter 9, p. 465.
3. [2] H.J. Hageman, in E. Müller (ed.), Methoden der Organischen Chemie, Houben-Weyl, G. Thieme Verlag, Stuttgart, 1975, Band IV/5b, Photochemie Teil II, p. 974.
4. [3] H.J. Hageman and W.G.B. Huysmans, Chem. Commun., (1969) 837.
5. [4] B.D. Sviridov, L.P. Gryzunova, V.M. Kuznets, G.A. Nikiforov, C.R.H.I. de Jonge, H.J. Hageman and V.V. Ershov, Izv. Akad. Nauk. SSSR, Ser. Khim., (1978) 2160.
6. [5] H.J. Hageman, in E. Müller (ed.), Methoden der Organischen Chemie, Houben-Weyl, G. Thieme Verlag, Stuttgart, 1975, Band IV/5b, Photochemie Teil II, p. 943.
7. [6] M. Sarakha, A. Rossi, G. Guyot and P. Boule, C.R. Acad. Sci., 307 (1988) 739. A. Seffar, G. Dauphin and P. Boule, Chemosphere, 16 (1987) 1205.
8. [6] M. Sarakha, A. Rossi, G. Guyot and P. Boule, C.R. Acad. Sci., 307 (1988) 739. A. Seffar, G. Dauphin and P. Boule, Chemosphere, 16 (1987) 1205.
9. [7] V.M. Kuznets, D.N. Shigorin and A.L. Buchachenko, Dokl. Akad. Nauk. SSSR, 234 (1977) 1112.
10. [8] V.M. Kuznets, P.P. Levin, I.V. Khudyakov and V.A. Kuzmin, Izv. Akad. Nauk. SSSR, Ser. Khim., (1978) 1284.
11. [9] V.M. Kuznets, A.Z. Yankelevich, B.D. Sviridov, G.A. Nikiforov, C.R.H.I. de Jonge, H.J. Hageman and V.V. Ershov, Izv. Akad. Nauk. SSSR, Ser. Khim., (1979) 1251.
12. [10] R. Bonneau, H. Moufid and G. Guyot, New. J. Chem., 15 (1991) 257.
13. [11] H.J. Hageman, in E. Müller (ed.), Methoden der Organischen Chemie, Houben-Weyl, G. Thieme Verlag, Stuttgart, 1975, Band IV/5b, Photochemie Teil II, p. 978.
14. [12] H.J. Hageman, in E. Müller (ed.), Methoden der Organischen Chemie, Houben-Weyl, G. Thieme Verlag, Stuttgart, 1975, Band IV/5b, Photochemie Teil II, p. 981.
15. [13] B.H. Bibo, Dissertation, T.U. Delft, 1969.
16. [14] P. Brassard and P. L'Ecuyer, Can. J. Chem., 36 (1958) 700.
17. [15] C.R.H.I. de Jonge, H.J. Hageman, G. Hoentjen and W.J. Mijs, Org. Synth. Coll. VI, (1988) 412.
18. [16] A.S. Hay, J. Org. Chem., 34 (1969) 1160.
19. [17] J.B. Conant and L.F. Fieser, J. Am. Chem. Soc., 45 (1923) 2194.
20. [18] A. McKillop, B.P. Swann and E.C. Taylor, Tetrahedron, 26 (1970) 4031.
21. [19] J.H. van Dijk, Z. Anal. Chem., 247 (1969) 262.
22. [20] J.H. van Dijk, Chimia, (1970) Suppl. 234.
23. [21] C.M. Orlando, H. Mark, A.K. Bose and M.S. Manhas, Chem. Commun., (1966) 714; J Am. Chem. Soc., 89 (1967) 6527; J Org. Chem., 33 (1968) 2512.
24. [21] C.M. Orlando, H. Mark, A.K. Bose and M.S. Manhas, Chem. Commun., (1966) 714; J Am. Chem. Soc., 89 (1967) 6527; J Org. Chem., 33 (1968) 2512.
25. [21] C.M. Orlando, H. Mark, A.K. Bose and M.S. Manhas, Chem. Commun., (1966) 714; J Am. Chem. Soc., 89 (1967) 6527; J Org. Chem., 33 (1968) 2512.
26. [22] K. Schimmelschmidt, Liebigs Ann. Chem., 566 (1950) 184.
27. [23] P.P. Levin, V.B. Luzhkov and A.P. Darmanyan, Izv. Akad. Nauk. SSSR, Ser. Khim., (1980) 1542.
28. [24] N.J. Bunce, J.E. Ridley and M.C. Zerner, Theor. Chim. Acta, 45 (1977) 283.
29. [25] N.J. Turro, Modern Molecular Photochemistry, Benjamin/Cummings, 1978, Chapter 10.
30. [26] R.C. Cookson, D.A. Cox and J. Hudec, J. Chem. Soc. (C), (1971) 3950.
31. [27] P. Yates, S.N. Ege, G. Büchi and D. Knutsen, Can. J. Chem., 45 (1967) 2927. S.N. Ege and P. Yates, Can. J. Chem., 45 (1967) 2933.
32. [27] P. Yates, S.N. Ege, G. Büchi and D. Knutsen, Can. J. Chem., 45 (1967) 2927. S.N. Ege and P. Yates, Can. J. Chem., 45 (1967) 2933.
33. [28] D. Bryce-Smith, R. Deshpande, A. Gilbert and J. Grzonka, Chem. Commun., (1970) 561.
34. [29] F.D. Lewis and R.W. Johnson, J. Am. Chem. Soc., 94 (1912) 8914.
35. [30] H.J. Hageman and U.E. Wiersum, unpublished observations, 1971. H.J. Hageman and U.E. Wiersum, Chem. Commun., (1971) 497.
36. [30] H.J. Hageman and U.E. Wiersum, unpublished observations, 1971. H.J. Hageman and U.E. Wiersum, Chem. Commun., (1971) 497.
37. [31] P.S. Dewar, A.R. Forrester and R.H. Thomson, J. Chem. Soc. (C), (1971) 3950.
38. [32] A. Feigenbaum, Y. Fort, J.P. Pete and D. Scholler, J. Org. Chem., 51 (1986) 4424.