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The reaction of chlorosulfonyl isocyanate with epoxides. A novel conversion of epoxides to cyclic carbonates
Author(s) -
Murthy K. S. Keshava,
Dhar D. N.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210630
Subject(s) - chemistry , isocyanate , yield (engineering) , hydrolysis , phenyl isocyanate , epoxide , organic chemistry , sequence (biology) , reaction conditions , polymer chemistry , polyurethane , catalysis , biochemistry , materials science , metallurgy
Abstract The facile reaction of chlorosulfonyl isocyanate (CSI) with epoxides is described. The initially formed 2‐chlorosulfonylimino‐1,3‐dioxolane 2a‐e and N ‐chlorosulfonyl‐1,3‐oxazolidin‐2‐one 3a‐e derivatives undergo smooth hydrolysis to yield the corresponding 1,3‐dioxolan‐2‐one 4a‐e and 1,3‐oxazolidin‐2‐one 5a‐e derivatives respectively. This reaction sequence provides a convenient one‐pot method for the conversion of epoxides to cyclic carbonates. Substrates such as 1g‐i are exceptions to this otherwise general reaction pathway.