Kinetic data and quantum chemical calculations show that monofluoroalkenes with vertical ionization potentials (IP) greater than 9.0 eV react with chlorosulfonyl isocyanate (CSI) via a concerted process.  Monofluoroalkenes with IP values less than 8.6 eV react with CSI by a dipolar stepwise pathway.  Competing pathways are expected for reactions of CSI and monofluoroalkenes with IP values between 8.6 and 9.0 eV.  Our data also provide evidence for a pre-equilibrium charge transfer complex on the reaction pathway.

Calculations and experimental data supporting both concerted and stepwise pathways for reaction of chlorosulfonyl isocyanate with monofluoroalkenes

243rd National Meeting (2012)

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