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., Unal A., ŞAHİN E., BOZKAYA U., KARA Y.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, cilt.15, ss.931-936, 2019 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 15
  • Basım Tarihi: 2019
  • Doi Numarası: 10.3762/bjoc.15.89
  • Dergi Adı: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.931-936
  • Anahtar Kelimeler: addition reaction, chlorosulfonyl isocyanate, sulfamoyl chloride, theoretical calculations, ACID
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.