136015-81-1Relevant academic research and scientific papers
Aluminum chloride catalyzed stereo- and regiospecific allylsilylation of alkynes: a convenient route to silyldienes
Yeon, Seung Ho,Han, Joon Soo,Hong, Eunkee,Do, Youngkyu,Jung, Il Nam
, p. 159 - 166 (2007/10/02)
Allyltrimethylsilane reacts with phenylalkynes in the presence of aluminum chloride catalyst under mild conditions to afford silylphenyldienes in moderate yield.In this allylsilylation reaction, the silyl group adds regioselectively to the terminal carbon and the allyl group to the inner carbon of the triple bond.The allylsilylation of phenylacetylene gives the allylsilylated product having the silyl and allyl groups in the cis-position, while diphenylacetylene gives the trans product.The allylic inversion was also observed in the allylsilylation with the stereohomogeneous (Z)-crotyltrimethylsilane.These results are consistent with the initial formation of trimethylsilyl cation intermediate and a stepwise process of allylsilylation.Keywords: Alkylsilylation; Alkynes; Allylic inversion; Allylsilanes; Stereoselectivity; Regioselectivity
Formation and Reactions of Olefins with Vicinal Silyl and Stannyl Substituents
Mitchell, T. N.,Wickenkamp, R.,Amamria, A.,Dicke, R.,Schneider, U.
, p. 4868 - 4874 (2007/10/02)
The silicon-tin bond in Me3SiSnR3 (R=Me, n-Bu) adds regio- and stereospecifically to 1-alkynes and also to a limited number of nonterminal alkynes when Pd(PPh3)4 is added as a catalyst.The use of the (Z)-silylstannylalkenes thus formed in synthesis either
