Chlorosulfonyl isocyanate (CSI) is a sluggish electrophile but reacts with many hydrocarbon and fluoroalkenes to give beta-lactam products.  For example, monofluoroalkenes like 2-fluoro-1-decene and disubstituted fluoroalkenes like 3-fluoro-3-hexene readily react with CSI to give beta-lactam products.  Terminal fluoroalkenes like 1-fluoro-1-decene do not react with CSI at temperatures below 70o C where the fluoro-beta-lactam products are stable.  Microwave initiation, or use of N-heterocyclic carbene (NHC) catalysts assist reactions of CSI with unreactive hydrocarbon and monofluoroalkenes.

Microwave initiation and catalysis of chlorosulfonyl isocyanate reactions with unreactive hydrocarbon and fluoroalkenes

243rd National Meeting (2012)

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