Vinyl-, allyl-, and phenylethynylsilanes. Effect of silicon on their reactions as dienophiles and the synthesis of phenylated phenyl-and benzylsilanes

ME Freeburger, L Spialter

Index: Freeburger,M.E.; Spialter,L. Journal of Organic Chemistry, 1970 , vol. 35, # 3 p. 652 - 657

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Citation Number: 27

Abstract

The Diels-Alder reaction of vinyl-, allyl-, and phenylethynylsilanes with tetraphenylcyclopentadienone was studied. In all cases, the reaction was slower than that of the carbon analogs. Allylsilanes gave the expected adducts, albeit slowly, but phenylethynylsilanes were generally unreactive, only phenylethynyltrimethylsilane affording an adduct. The reaction of vinylsilanes was complicated by the fact that the ...