08-01-2021-0218 - Sulphene–tertiary amine zwitterions: intermediates in the multiexchange of hydrogen in a sulphene reaction

 Issue 23, 1972

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  Journal of the Chemical Society, Chemical Communications

Sulphene–tertiary amine zwitterions: intermediates in the multiexchange of hydrogen in a sulphene reaction 

J. F. King,   E. A. Luinstra  and  D. R. K. Harding  

Abstract

With sterically unhindered tertiary amines and deuterium oxide or other deuteriated sulphene traps, alkanesulphonyl halides with more than one α-hydrogen may yield products having more than one of the α-hydrogens exchanged; evidence is presented for a mechanism involving reaction of the intermediate sulphene with the amine to form a zwitterion ([graphic omitted]HR1SO2[graphic omitted]R32) which may then exchange hydrogens viaits conjugate acid.

https://pubs.rsc.org/en/content/articlelanding/1972/C3/C39720001313