Intramolecular Cyclization of 4-[3-(Trimethylsilyl)prop-1-en-1-yI]-cyclohexanecarbaldehyde with Loss of Formyl Carbon

Article abstract of DOI:10.1246/bcsj.71.1639

Treatment of cis- and trans-4-[3-(trimethylsilyl)prop-1-en-1-yl]cydohexanecarbaldehyde (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 deformyhition 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.