Journal of the Chemical Society. Perkin transactions II p. 903 - 906 (1989)
Update date:2022-09-26
Topics:
Armesto, Diego
Horspool, William M.
Langa, Fernando
The acetophenone-sensitised irradiation of a series of 1-aryl-4,4-dimethyl-6,6-diphenyl-2-azahexa-2,5-dienes has been carried out.All undergo an aza-di-?-methane rearrangement to yield a cyclopropylimine.The determination of the quantum yields for the rearrangement showed a dependence on the nature of the substituents on the N-benzyl group and the reaction is most efficient with electron-withdrawing substituents.The linear relationship between log φ and ?+ suggests that there is an homoconjugative interaction between the benzyl group and the nitrogen ione-pair.
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