The Journal of Organic Chemistry

Peptide synthesis with benzo-and naphthosultones

F Acher, M Wakselman

Index: Acher, Francine; Wakselman, Michel Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4133 - 4138

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Citation Number: 16

Abstract

6-Nitro-and 6, 8-dinitronaphth [1, 8-cd]-1, 2-oxathiole S, S-dioxides (7p and 7c) have been prepared from the parent naphthosultone 7a and compared with 5-nitrobenz [l, 6-d]-3H-1, 2- oxathiole S, S-dioxide (lb) as coupling reagents for peptide synthesis. Nucleophilic attack of a carboxylate salt on these strained five-membered sultones leads to activated esters 3 and 9 which rapidly react with amines (except in the case of 9c). The rate constant for the ...