Tetrahedron

An effective synthesis of N-substituted 2-sulfenamoylbenzoates and 1, 2-benzisothiazolin-3-ones that uses 1, 2-benzisothiazolin-3-one as a leaving group

M Shimizu, Y Sugano, T Konakahara, Y Gama…

Index: Shimizu, Masao; Sugano, Yoshinori; Konakahara, Takeo; Gama, Yasuo; Shibuya, Isao Tetrahedron, 2002 , vol. 58, # 19 p. 3779 - 3783

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Citation Number: 23

Abstract

N-Substituted 2-sulfenamoylbenzoates and 1, 2-benzisothiazolin-3-ones were effectively synthesized by the substitution reaction between S-[2-(3-oxo-1, 2-benzisothiazolinyl)]-2- mercaptobenzoates (2) and primary amines. The substitution reaction occurred on the sulfur atom of the 2-sulfenamoyl group of 2, and 1, 2-benzisothiazolin-3-one behaved as a leaving group. The eliminated 1, 2-benzisothiazolin-3-one could be reused as a starting material ...