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Paper | Regular issue | Vol 41, No. 5, 1995, pp.921-930
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6944
Conversion of Dihydro-1,4-oxathiin-3-carboxamide to the Isomeric Dihydro-1,4-oxathiin-2-carboxamide

Hoh-Gyu Hahn,* Kee-Hyuk Chang, and Wha Suk Lee

*Organic Chemistry Laboratory, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, 130-650, Seoul, Korea

Abstract

The preparation of isomeric dihydro-1,4-oxathiin (3) from the dihydro-1,4-oxathiin (1) via dichloro-1,4-oxathiane (4) is described. Chlorination of 1 followed by treatment of the resulting dichloride (4) with aqueous acetone gave dihydroxy-1,4-oxathiin (5). The solvolysis to produce intermediate chlorohydrin (11) was favored relative to elimination reaction to give exomethylene compound (8). Dehydration of 5 followed by reduction afforded α-hydroxy-1,3-oxathiolane (2) which is a key compound to prepare the isomeric dihydro-1,4-oxathiin (3). The reason for more facile displacement of chlorine at C-2 in comparison with that at C-3 in 4 was also discussed.