Chlorodimethylsulfonium Chloride–Mediated Formation of Phenyl-α-chloroazoalkanes

Abstract

Phenylhydrazones (1) are efficiently converted into phenyl-α-chloroazoalkanes (2) upon treatment with chlorodimethylsulfonium chloride. Pendent olefins, silyl ethers, and the phenyl ring of the hydrazone are stable to these reaction conditions.

Keywords:

• Activated DMSO
• aryl-α-chloroazoalkanes
• chlorodimethylsulfonium chloride
• hydrazone
• oxidation
• phenylhydrazone

ACKNOWLEDGMENTS

This material is based upon work supported by the National Science Foundation under Grant CHE-0748058. Financial support from the University of Vermont is gratefully acknowledged. Support from the Vermont Experimental Program to Stimulate Competitive Research (Grant EPS0236976) is gratefully acknowledged. M. B. thanks Amgen for financial support in the form of a new faculty award. S. J. thanks the Hughes Endeavor for Life Science Excellence (HELiX) for support in the form of a minigrant.