Intramolecular Cyclization of 4-[3-(Trimethylsilyl)prop-1-en-1-yl]cyclohexanecarbaldehyde with Loss of Formyl Carbon
作者： Chiaki Kuroda , Atsushi Murase , Hideyuki Suzuki , Toru Endo , Shuzo Anzai
DOI: 10.1246/BCSJ.71.1639
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摘要: Treatment of cis- and trans-4-[3-(trimethylsilyl)prop-1-en-1-yl]cyclohexanecarbaldehyde (2a 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 2a, b to 1 takes place under basic conditions before cyclization 3. also shown allylsilane carbonyl does not proceed via an eclipsed conformation.
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