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Communication | Special issue | Vol 52, No. 3, 2000, pp.1025-1028
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S119
Substituent Effects on the Stereochemical Course of Electrophile-initiated Tetrahydropyran-forming Reactions: A Possible Stereoelectronic Effect

David J. Hart,* Suzanne Patterson, and Alain Zakarian

*Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, U.S.A.


A series of 4-penten-1,3-diol derivatives were prepared and treated with phenylselenenyl chloride to provide tetrahydropyrans. The stereochemical course of the reactions is consistent with a chair-like transition state in which the oxygen substituent at the 3-position largely occupies an axial site. A structurally related 3-methyl-4-penten-1-ol derivative gave a major product consistent with a chair transition state in which the methyl group occupies an equatorial site.