The Journal of Organic Chemistry

Silane reductions in acidic media. V. Reductions of alkyl-substituted cyclohexanones by di-and tri-tert-butylsilanes. Steric hindrance to nucleophilic attack at silicon in …

MP Doyle, CT West

文献索引：Doyle,M.P.; West,C.T. Journal of Organic Chemistry, 1975 , vol. 40, p. 3829 - 3834

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被引用次数: 17

摘要

Results Di-tert-butylmethylsilane. The reactions of alkyl-substituted cyclohexanones with di- tert-butylmethylsilane are significantly and unexpectedly faster than those with ditert- butylsilane. Using 6.6 equiv of trifluoroacetic acid, reductions of 4-tert-butyl, 4-methyl-, 2- methyl-, and even 3, 3, 5-trimethylcyclohexanone are complete within 20 hr at room temperature. Di-tert-butylmethylsilane is 20 to 40 times more reactive than di-tert- ...