Tetrahedron

N-hydroxypyridine-2-thione carbamates. IV. A comparison of 5-exo cyclizations of an aminyl radical and an aminium cation radical

M Newcomb, TM Deeb, DJ Marquardt

Index: Newcomb, Martin; Deeb, Thomas M.; Marquardt, Donald J. Tetrahedron, 1990 , vol. 46, p. 2317 - 2328

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Citation Number: 84

Abstract

Cyclizations of the N-butyl-4-pentenaminyl radical and the N-butyl-4-pentenaminium cation radical were studied. The radicals were produced in chain reactions from the same N- hydroxypyridine-2-thione carbamate precursor. Rate constants for cyclization of the aminyl radical and ring opening of the product thus formed at 50° C were determined. Cyclizations of the aminium cation radical, formed by protonation of the aminyl radical, were studied ...