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Paper | Regular issue | Vol 31, No. 12, 1990, pp.2219-2224
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5597
Oxidation Chemistry of cis-2-(3-Furylidene)ethanol

William E. Fristad and Leo A. Paquette*

*Evans Chemical Laboratories, The Ohio State University, 120 W. 18th Avenue, Columbus, Ohio 43210, U.S.A.


Submission of the tri-n-butylstannylmethyl ether (9) of furylcarbinol (8) to Still rearrangement leads stereoselectively to 10 as the exclusive product. The cis-oriented nature of the hydroxyethyl and 3-furyl functional groups in 10 is cause for ready ring closure either to bensofuran (10) or lactone (13) depending upon conditions.