Mechanism of the photochemical Wolff rearrangement. The role of conformation in the photolysis of. alpha.-diazo carbonyl compounds
H Tomioka, H Okuno, Y Izawa
Index: Tomioka, Hideo; Okuno, Hiroshi; Izawa, Yasuji Journal of Organic Chemistry, 1980 , vol. 45, # 26 p. 5278 - 5283
Full Text: HTML
Citation Number: 59
Abstract
Investigation of photochemical processes of several a-diazo carbonyl compounds reveals that the Wolff rearrangement, to form ketene takes place directly from the singlet excited state of the s-2 conformer whereas the excited state of the sE conformer dissociates nitrogen to generate singlet carbonyl carbene, which either undergoes characteristic carbenic reactions, eg, insertion and 1, 2-hydrogen shift, or gives rise to ketene. The migratory ...
Related Articles:
[Davis, Charles R.; Swenson, Dale C.; Burton, Donald J. Journal of Organic Chemistry, 1993 , vol. 58, # 24 p. 6843 - 6850]
[Madder, Annemieke; Sebastian, Sonny; Van Haver, Dirk; De Clercq, Pierre J.; Maskill, Howard Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 12 p. 2787 - 2793]
The Synthesis of a β-Methylene-γ-spirolactone
[Petraganani,N. et al. Synthesis, 1977 , p. 112 - 113]
The Synthesis of a β-Methylene-γ-spirolactone
[Petraganani,N. et al. Synthesis, 1977 , p. 112 - 113]
Electrochemical coupling of activated olefins and alkyl dihalides: formation of cyclic compounds
[Lu, Yu-Wei; Nedelec, Jean-Yves; Folest, Jean-Claude; Perichon, Jacques Journal of Organic Chemistry, 1990 , vol. 55, # 8 p. 2503 - 2507]