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

Autor: Aytekin Köse, Aslı Ünal, Ertan Şahin, Uğur Bozkaya, Yunus Kara
Jazyk: angličtina
Rok vydání: 2019
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 15, Iss 1, Pp 931-936 (2019)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.15.89
Popis: 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.
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