Tetrahedron

[2, 3]-Sigmatropic rearrangements of didehydropiperidinium ylids

JB Sweeney, A Tavassoli, NB Carter, JF Hayes

Index: Sweeney; Tavassoli, Ali; Carter, Neil B.; Hayes, Jerome F. Tetrahedron, 2002 , vol. 58, # 51 p. 10113 - 10126

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Citation Number: 33

Abstract

The [2, 3]-sigmatropic rearrangements of ammonium ylids derived from 1, 2, 5, 6- tetrahydropyridine have been studied: both rearrangement and elimination processes are observed, with rearrangement favoured when aprotic solvents are used in the reaction. The presence of anion-stabilizing substituents on the nucleophilic carbon atom of the intermediate ylid species involved in the tranformation also engenders rearrangement; ...