211995-99-2Relevant articles and documents
Intramolecular Cyclization of 4-[3-(Trimethylsilyl)prop-1-en-1-yI]-cyclohexanecarbaldehyde with Loss of Formyl Carbon
Kuroda, Chiaki,Murase, Atsushi,Suzuki, Hideyuki,Endo, Toru,Anzai, Shuzo
, p. 1639 - 1647 (2007/10/03)
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.