Tetrahedron Letters

Isomerization reactions of lithium N-butyl-4-pentenylamide

M Newcomb, MT Burchill

Index: Newcomb, Martin; Burchill, Michael T. Tetrahedron Letters, 1982 , vol. 23, # 47 p. 4867 - 4870

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Abstract

Abstract Lithium N-butyl-4-pentenylamide (1) in tetrahydrofuran at 22 C rearranged smoothly to give a mixture (after protonation) of 1-butyl-2-methylpyrrolidine, formed by an unusual cyclization process, and cis-and trans-N-butyl-3-pentenylamine; in the presence of 2.0 molar equiv of hexamethylphosphoramide, the total rate of isomerization was accelerated by a factor of 2.5.

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