Unique reaction of cyclicimides containing double bond with chlorosulfonyl isocyanate and theoretical computations: Solvent-free reactions

The addition reactions of chlorosulfonyl isocyanate (CSI) to N-phenylmaleimide and 2-phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione were investigated. Interesting products were obtained from the re-action of both compounds with CSI. N-phenylmaleimide led to the formation of an electrophilic substitu-tion product, 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzenesulfonyl chloride while 2-phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione led to the formation of ((3aS,7aR,E)-3-oxo-2-phenyl-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chloride. The structure of both products was determined by using spectroscopic methods such as NMR and Mass. Theoretical studies were carried out to explain the different reactions of both compounds with similar structures. It was determined by theoretical stud-ies that the progression of both compounds through different reactions depends on the structure of the imides used and the energy levels of the intermediates.(c) 2022 Elsevier B.V. All rights reserved.

Journal

JOURNAL OF MOLECULAR STRUCTURE

Year

2023

Volume

1274

ISSN

0022-2860

eISSN

1872-8014

DOI

10.1016/j.molstruc.2022.134428

WoS UID

WOS:000904618500004