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Communication | Regular issue | Vol 27, No. 4, 1988, pp.867-870
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4433
Preparation of 1-Tosyl-2- and 3-Pyrrolidinones via Ketenes and Carbenes

Antonio Saba* and Antonio Selva

*Department of Chemistry, University of Sassari, Via Vienna 2, I-07100 Sassari, Italy

Abstract

Catalytic decomposition of 1-diazo-4-tosylamino-2-butanone 1a, -2-pentanone 1b, and -2-hexanone 1c, results in the quantitative formation of the 1-tosyl-3-pyrrolidinones 2a, 2b and 2c, while the photolysis afforded the rearranged esters, 3a, 3b and 3c, or the unexpected 1-tosyl-2-pyrrolidinones 4a, 4b and 4c depending on the solvent employed.