Photolytic decomposition of some polycyclic α-diazoketones: Generation and reactivity of 1,2-oxocarbenes in benzene with and without tert-butylamine

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 11, 1996, Pages 2303-2307

  Brown, Peter J N ^a   Cadogan, J I G ^b   Gosney, Ian ^c   Johnstone, Alexander ^c   Michael Paton, R ^c   Wilson, Norman H ^c  

^a BP EXPLORATION   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005746392     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/P29960002303     Document Type: Article

References (10)

1. C. F. Bannerman, P. J. N. Brown, J. I. G. Cadogan, I. Gosney, A. Johnstone and N. H. Wilson, J. Chem. Soc., Chem. Commun., 1975, 618.
2. For a review on the Wolff rearrangement, including mechanism and competing reactions, see G. B. Gill, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and G. Pattenden, Pergamon Press, Oxford, 1991, vol. 3, p. 887.
3. See, W. Reid and H. Lohwasser, Liebigs Ann. Chem., 1965, 683, 118, for details of the failure of 2-diazoacenaphthen-1-one 1 to undergo Wolff rearrangement on thermolysis, instead giving the corresponding ketazine.
4. B. M. Trost and P. L. Kinson, J. Am. Chem. Soc., 1975, 97, 2438.
5. M. Periasamy and M. V. Bhatt, Synthesis, 1977, 330.
6. W. E. Barth and R. G. Lawton, J. Am. Chem. Soc., 1971, 93, 1730.
7. J. Douris and A. Mathieu, Bull. Soc. Chim. Fr., 1971, 3365.
8. M. E. Alonso, A. Morales and A. W. Chitty, J. Org. Chem., 1982, 47, 3747.
9. R. M. Paton and R. U. Weber, Org. Magn. Res., 1977, 9, 494.
10. W. Reid and R. Dietrich, Chem. Ber., 1961, 94, 387.