Abstract
Abstract Treatment of cis- and trans-4-[3-(trimethylsilyl)prop-1-en-1-yl]cyclohexanecarbaldehyde (2a and 2b) with tetrabutylammonium fluoride in dilute tetrahydrofuran afforded 7-vinylbicyclo[2.2.1]heptan-1-ol (3), the same product obtained from 4-[3-(trimethylsilyl)prop-1-en-1-yl]cyclohexanone (1). It was found that oxidative deformylation of 2a, b to 1 takes place under basic conditions before the cyclization to 3. It was also shown that cyclization of allylsilane with carbonyl does not proceed via an eclipsed conformation.
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