THE AZA-DI-PI-METHANE REARRANGEMENT OF BETA,GAMMA-UNSATURATED OXIMES

Authors
ARMESTO D RAMOS A MAYORAL EP
Citation
D. Armesto et al., THE AZA-DI-PI-METHANE REARRANGEMENT OF BETA,GAMMA-UNSATURATED OXIMES, Tetrahedron letters, 35(22), 1994, pp. 3785-3788
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
22
Year of publication
1994
Pages
3785 - 3788
Database
ISI
SICI code
0040-4039(1994)35:22<3785:TAROBO>2.0.ZU;2-5
Abstract
Although previous studies have shown that ocyclic beta,gamma-unsaturat ed oximes and oxime ethers do not undergo the aza-di-pi-methane (ADPM) rearrangement, the 2-methyl-4,4-diphenyl-2-vinylbut-3-enal oxine 5a, its methyl ether 5b and the 2,2,4,4-tetraphenylbut-3-enal oxime 14 giv e the corresponding cyclopropyl derivatives 8a. 8b and 15 by the ADPM path, in a reaction that is controlled by the stability of the interme diate 1,3-biradical.