The aza-di-π-methane rearrangement of β-γ-unsaturated oximes

D Armesto, A Ramos, EP Mayoral

Index: Armesto, Diego; Ramos, Ana; Mayoral, Elena P. Tetrahedron Letters, 1994 , vol. 35, # 22 p. 3785 - 3788

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Citation Number: 15

Abstract

Abstract Although previous studies have shown that acyclic β, γ-unsaturated oximes and oxime ethers do not undergo the aza-di-π-methane (ADPM) rearrangement, the 2-methyl-4, 4-diphenyl-2-vinylbut-3-enal oxime 5a, its methyl ether 5b and the 2, 2, 4, 4-tetraphenylbut-3- enal oxime 14 give the corresponding cyclopropyl derivatives 8a, 8b and 15 by the ADPM path, in a reaction that is controlled by the stability of the intermediate 1, 3-biradical.