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Communication | Regular issue | Vol 19, No. 5, 1982, pp.829-835
Published online, 1st January, 1970
DOI: 10.3987/R-1982-05-0829
Selective Cleavage of Unsymmetrical 2,2-Spiro-1,3-dioxolanes I. Ketalization of 5-Bromo-3-methoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]furan-4-one and Its Analogs

Makiko Sakai

*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan

Abstract

Reaction of 2-bromocyclohexanones fused with an aromatic or heteroaromatic ring (1-4) with epibromohydrin or 3-bromo-1,2-propanediol gave two (a and b) or four (a, b, c, and d) isomers of the corresponding 2,2-spiro-4-bromomethyl-1,3-dioxolanes 5-8, respectively. The stereochemistry of the reactions is discussed.