Thio- and seleno-lactonizations of alkynoic acids
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1999-2004
- https://doi.org/10.1039/p19860001999
Abstract
Regio- and stereo-specific thio- and seleno-lactonizations of hept-4-ynoic acid (1a), hex-4-ynoic acid (1b), and pent-4-ynoic acid (1c) can be achieved by treatment of benzenesulphenyl chloride and benzeneselenenyl chloride using a hydrogen chloride capture such as triethylamine or a better capture in most cases, 3,4-dihydro-2H-pyrido[1,2a]pyrimidin-2-one. N-Phenylselenophthalimide is also effective for the selenolactonization, although E and Z lactones (E)-(2c; X = Se) and (Z)-(2c; X = Se) are formed from (1c). Cleavage reactions of γ-alkylidene-γ-butyrolactones afford a new preparative method for 4-oxoalkanoic acid derivatives.Keywords
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