Photochemistry of Diaryl Vicinal Tetraketones and Chemistry of Intermediate (Aroyloxy)arylketenes

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 480-488

  Rubin, Mordecai B ^a   Etinger, Marina ^a   Kapon, Moshe ^a   Krochmal Jr , Eric C ^a   Monosov, Raisa ^a   Wierlacher, Stephan ^b,c   Sander, Wolfram ^b,c  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^c RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0346649588     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971247q     Document Type: Article

References (37)

1. A prelimnary report of part of this work has appeared. Rubin, M. B.; Krochmal, E. C., Jr.; Kaftory, M. Rec. Trav. Chim. 1979, 98, 85. Taken in part from the M.Sc. thesis of M. Etinger, Technion, 1995.
2. For reviews see Rubin, M. B. Top. Curr. Chem. 1969, 13, 251. Monroe, B. M. Adv. in Photochem. 1971, 8, 77. Rubin, M. B. Top. Curr. Chem. 1985, 129, 1.
3. For reviews see Rubin, M. B. Top. Curr. Chem. 1969, 13, 251. Monroe, B. M. Adv. in Photochem. 1971, 8, 77. Rubin, M. B. Top. Curr. Chem. 1985, 129, 1.
4. For reviews see Rubin, M. B. Top. Curr. Chem. 1969, 13, 251. Monroe, B. M. Adv. in Photochem. 1971, 8, 77. Rubin, M. B. Top. Curr. Chem. 1985, 129, 1.
5. Netto-Ferreira, J. C.; Scaiano, J. C. Photochem. Photobiol. 1991, 54, 17.
6. Rubin, M. B.; Heller, M.; Monisov, R.; Gleiter, R.; Dörner, T. J Photochem. Photobiol. A: Chem. 1995, 87, 7.
7. Abenius, P. W.; Soderbaum, H. G. Ber. 1891, 24, 3033.
8. For a general review of the chemistry of vicinal polyketones see Rubin, M. B. Chem. Rev. 1975, 75, 177.
9. Horner, L.; Maurer, F. Ann. 1970, 736, 145. Idem. Chem. Ber. 1968, 101, 1783.
10. Horner, L.; Maurer, F. Ann. 1970, 736, 145. Idem. Chem. Ber. 1968, 101, 1783.
11. Fischer, E. (deceased), Weizmann Institute, personal communication.
12. Diphenyl tetraketone: Beddoes, R. L.; Cannon, J. R.; Heller M.; Mills, O. S.; Patrick, V. A.; Rubin, M. B.; White, A. H. Aust. J. Chem. 1982, 35, 543. Dimesityl tetraketone: Kaftory, M.; Rubin, M. B. J. Chem. Soc., Perkin Trans. 2 1983, 149
13. Diphenyl tetraketone: Beddoes, R. L.; Cannon, J. R.; Heller M.; Mills, O. S.; Patrick, V. A.; Rubin, M. B.; White, A. H. Aust. J. Chem. 1982, 35, 543. Dimesityl tetraketone: Kaftory, M.; Rubin, M. B. J. Chem. Soc., Perkin Trans. 2 1983, 149
14. The equlibrium constant for hydration of 1a to its monohydrate in dioxane containing traces of water at 25°C has been determined to be on the order of 1000, M. Heller, M. Sc. thesis, Technion.
15. Gleiter, R.; Kramer, R.; Irngartinger, H.; Bissinger, C. J. Org. Chem. 1992, 57, 252.
16. Kramer, R., Technion, unpublished results.
17. Kaftory, M. Acta Crystallogr. 1979, B35, 1717.
18. Total light intensity on a 0.9 × 2.7 cm area of the cell.
19. Evans, D. J. Chem. Soc. 1957, 1351. Lewis, G. N.; Kasha, M. J. Am. Chem. Soc. 1944, 66, 2100.
20. Evans, D. J. Chem. Soc. 1957, 1351. Lewis, G. N.; Kasha, M. J. Am. Chem. Soc. 1944, 66, 2100.
21. Sammes, P. G. Tetrahedron, 1976, 32, 405. For a recent reference see Hopf, H.; Laue, T.; Zander, M. Angew. Chem., Intl. Ed. Engl. 1991, 30, 432.
22. Sammes, P. G. Tetrahedron, 1976, 32, 405. For a recent reference see Hopf, H.; Laue, T.; Zander, M. Angew. Chem., Intl. Ed. Engl. 1991, 30, 432.
23. For a summary see Rubin, M. B. Top. Curr. Chem. 1985, 129, 1.
24. The initial H-atom abstraction need not be by the carbonyl group adjacent to the aromatic ring since there will be a rapid equilibrium between ketyl radicals.
25. Dominguez, F.; Cava, M. P. Tetrahedron Lett. 1982, 5513.
26. Griffin, G. W.; O'Connell, E. J. J. Am. Chem. Soc. 1962, 84, 4148. Zimmerman, H. E.; Durr, H. G. C.; Lewis, R. G.; Bram, S. Ibid. 1962, 84, 4149. Barik, R.; Bhatttacharya, K.; Das, P. K.; George, M. V. J. Org. Chem. 1986, 51, 3420 and references therein.
27. Griffin, G. W.; O'Connell, E. J. J. Am. Chem. Soc. 1962, 84, 4148. Zimmerman, H. E.; Durr, H. G. C.; Lewis, R. G.; Bram, S. Ibid. 1962, 84, 4149. Barik, R.; Bhatttacharya, K.; Das, P. K.; George, M. V. J. Org. Chem. 1986, 51, 3420 and references therein.
28. Griffin, G. W.; O'Connell, E. J. J. Am. Chem. Soc. 1962, 84, 4148. Zimmerman, H. E.; Durr, H. G. C.; Lewis, R. G.; Bram, S. Ibid. 1962, 84, 4149. Barik, R.; Bhatttacharya, K.; Das, P. K.; George, M. V. J. Org. Chem. 1986, 51, 3420 and references therein.
29. Rubin, M. B.; Patyk, A.; Sander, W. Tetrahedron Lett. 1988, 29, 6641.
30. These radicals might be close to one another in a solvent cage.
31. For summaries of ketene chemistry see: Borrman, D. Methoden der Organsichen Chemie (Houben-Weyl), 4th ed.; Georg Thieme Verlag: Stuttgart, 1968; vol VII/4. Tidwell, T. Ketenes; Wiley: Chichester, 1995.
32. M. Kapon has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
33. Kuhn, H. J.; Braslavsky, S. E.; Schmidt, R. Pure Appl. Chem. 1989, 61, 198. Cf also Wintgens, V.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1988, 110, 511.
34. Kuhn, H. J.; Braslavsky, S. E.; Schmidt, R. Pure Appl. Chem. 1989, 61, 198. Cf also Wintgens, V.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1988, 110, 511.
35. Angus, W. R.; Owen, R. P. J. Chem. Soc. 1943, 227 reported isolation of a compound mp 115°C from reaction of mandelic acid and benzoyl chloride to which they assigned the structure 9d. Repetition of this procedure in our hands afforded a product of similar melting point which, however, could be shown by spectroscopic properties to be impure benzoic acid and could be purified by recrystallization to give pure benzoic acid, mp 122°C, identical with an authentic sample.
36. Freudenberg, K.; Markert, L. Chem. Ber. 1925, 58, 1758.
37. Barthel, W. F.; Leon, J.; Hall, S. A. J. Org. Chem. 1954, 19, 485.