Hydrosilylation of α,β-unsaturated nitriles and esters catalyzed by tris (triphenylphosphine)chlororhodium

Iwao Ojima, Miyoko Kumagai, Yoichiro Nagai

doi:10.1016/s0022-328x(00)87057-6

Hydrosilylation of α,β-unsaturated nitriles and esters catalyzed by tris (triphenylphosphine)chlororhodium

DOI Web Site Web Site 被引用文献5件

書誌事項

公開日: 1976-05

権利情報

https://www.elsevier.com/tdm/userlicense/1.0/

DOI

10.1016/s0022-328x(00)87057-6

公開者: Elsevier BV

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説明

Abstract The hydrosilylation of α,β-unsaturated nitriles and esters such as acrylonitrile, crotononitrile, cinnamonitrile, ethyl and methyl acrylate, ethyl and methyl crotonate and ethyl and methyl methacrylate using tris(triphenylphosphine)chlororhodium as a catalyst is described. The hydrosilylation of α,β-unsaturated nitriles provided α-adduct exclusively in high yield except in the case of trichlorosilane which afforded β-adduct with acrylonitrile. On the other hand, the hydrosilylation of α,β-unsaturated esters gave rather complex results. The selectivity of the reactions was dramatically affected by the substituent of the ester group and that on the β-carbon. Thus, the hydrosilylation of ethyl acrylate with triethylsilane afforded a β-adduct, but, that of ethyl crotonate using the same hydrosilane gave a 1,4-adduct exclusively. Possible mechanisms for these reactions are discussed.