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Report | Regular issue | Vol 22, No. 8, 1984, pp.1779-1788
Published online, 1st January, 1970
DOI: 10.3987/R-1984-08-1779
Formation and Reactions of Trichloro-γ-lactones

Seiichi Takano,* Shin’ichi Nishizawa, Masashi Akiyama, and Kunio Ogasawara

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

The allyl trichloroacetates, (6) and (7), have been converted into the trichloro-γ-lactones, (8) and (9), by cuprous chloride. On dechlorination using tri-n-butyltin hydride, regioselective reaction has occurred initially at α position to convert the trichlorides, (8) and (9), into the dichlorides, (11) and (12), which in turn have been converted into the rnonochlorides, (13) and (14), depend on amount of the reducing agent. On dehydrochlorination, both the trichlorides, (8) and (9), have furnished the dihalobutenolides, (16) and (17), via 1,2-elimination with DBU, while the monohalides, (13) and (14), have yielded the cyclopropa[2,3]butyrolactones, (26) and (27), via 1,3-elimination with potassium tert-butoxide.