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Article

A Simple Method for the Preparation of N-Sulfonylsulfilimines from Sulfides^†

Supporting Info

Andreas L. Marzinzik^‡ and K. Barry Sharpless*

Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037

J. Org. Chem., 2001, 66 (2), pp 594–596

DOI: 10.1021/jo0012039

Publication Date (Web): January 4, 2001

†

Dedicated to Carl R. Johnson for for his pioneering work on the fascinating and important chemistry of sulfilimines.

‡

Novartis Pharma AG, CH-4002 Basel, Switzerland.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sharples@scripps.edu

Abstract

While excellent methods exist for the oxidation of sulfides to sulfoxides R¹R²S → R¹R²SO, the aza-version of this atom transfer redox process, i.e., R¹R²S → R¹R²SN−SO₂R³, has been less reliable. In sulfilimine synthesis, sulfoxide has been an inevitable byproduct in all cases to date, and the yields of sulfilimine have varied widely. A nearly ideal procedure for the sulfide to sulfonyl sulfilimine transformation is described. Almost quantitative yields are achieved from a diverse set of sulfides and a broad range of the readily available sulfonyl nitrenoid sources known as chloramine salts (R³SO₂NClNa), essentially by simply stirring them together in acetonitrile.

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Published In Issue January 26, 2001
Received August 7, 2000

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Article

A Simple Method for the Preparation of N-Sulfonylsulfilimines from Sulfides^†