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, AYTEKİN; ÜNAL, ASLI; ŞAHİN, Ertan; BOZKAYA, UĞUR; KARA, Yunus

doi:10.3762/bjoc.15.89

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, cilt.15, ss.931-936, 2019 (SCI-Expanded)

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
Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
Hacettepe 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.