Tetrahedron Letters

A general anionic mechanism for thermodynamic control of regioselectivity in N-alkylation and acylation of heterocycles

TW Bentley, RVH Jones, PJ Wareham

Index: Bentley, T. William; Jones, Ray V.H.; Wareham, Peter J. Tetrahedron Letters, 1989 , vol. 30, # 30 p. 4013 - 4016

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Citation Number: 22

Abstract

Abstract Regioselective alkylation of 1, 2, 4-triazole (Ia, IIa) to 1-alkyl derivatives (Ib) may occur by nucleophilic displacement of the triazole anion, is thermodynamically-controlled (shown by a free energy diagram), and the position of equilibrium is relatively insensitive to the nature of the alkyl group.