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Communication | Regular issue | Vol 29, No. 3, 1989, pp.435-440
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4829
Synthesis of 2,2-Disubstituted Succinimides and Their Regioselective Thiocarbonylation Reaction

Yoshiyuki Kosugi,* Masako Kosugi, and Fumiko Hamaguchi

*Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


2,2-Dialkoxy- and 2,2-bis(alkylthio)succinimide (3a-c and 3g) were prepared from 2,3-dibromosuccinimide by the reaction with alkoxide or thiolate anion. In contrast to most 2,2-disubstituted succinimides, thiocarbonylation reaction of the imides bearing ethylenedioxy group with Lawesson reagent occurred at the more hindered carbonyl group to give monothioimides (6c and 6d) as major products.