An Anomalous Addition Of Chlorosulfonyl Isocyanate To A Carbonyl Group: The Synthesis Of ((3As,7Ar,E)-2-Ethyl-3-Oxo-2,3,3A,4,7,7A-Hexahydro-1H-Isoindol-1-Ylidene)Sulfamoyl Chloride

Abstract

In this study, we developed a new addition reaction of chlorosulfonyl isocyanate (CSI), starting from 2-ethyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione. The addition reaction of CSI with 2-ethyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione resulted in the formation of ylidenesulfamoyl chloride, whose exact configuration was determined by X-ray crystal analysis. We explain the mechanism of product formation supported by theoretical calculations.