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


KÖSE A., ÜNAL A. , ŞAHİN E., BOZKAYA U. , KARA Y.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol.15, pp.931-936, 2019 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 15
  • Publication Date: 2019
  • Doi Number: 10.3762/bjoc.15.89
  • Title of Journal : BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  • Page Numbers: pp.931-936

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.