K. Iwai, H. Kosugi, H. Uda
Apr 12, 1977
Citations
0
Influential Citations
66
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
A combination of the reaction of dianions of (phenylthio) acetic acid and its homologs with epoxides, the conjugate addition reaction of 3-phenylthio-2-(5H)-furanones with carbanion species, and the α-alkylation reaction of α-phenylthio-γ-butyrolactones is shown to provide a general method for the synthesis of a variety of substituted α-phenylthio-γ-butyrolactones. Oxidation of these α-phenylthiolactones to the corresponding sulfoxides, followed by pyrolysis furnishes all the types of substituted (3-, 4-, and 5-mono-; 3,4-, 3,5- 4,5-, and 5,5-di-; 3,4,5-tri-) 2(5H)-furanones in good overall yields.