Tetrahedron Letters

An explanation for the failure of aminomethanesulfonic acid to form sulfonamides. Acyl chloride-promoted generation of α-carboxamidoalkylating electrophiles.

GR Moe, LM Sayre, PS Portoghese

Index: Moe, Gregory R.; Sayre, Lawrence M.; Portoghese, Philip S. Tetrahedron Letters, 1981 , vol. 22, # 6 p. 537 - 540

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Citation Number: 16

Abstract

Abstract Attempted N, N-dibenzoylation of aminomethanesulfonic acid results in C S bond cleavage, generating synthetically useful α-benzamidomethylating electrophiles. The importance of this observation in regard to the reported failures to prepare sulfonamide analogs of peptides is discussed.