Synthesis and desilylation of some bis(trimethylsilyl)alkenes and polymers bearing bis(silyl)alkenyl groups |
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Authors: | Kazem D Safa Mina Namvari Shahin Tofangdarzadeh |
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Institution: | a Organosilicon Research Laboratory, Faculty of Chemistry, University of Tabriz, 51664 Tabriz, Iran b Research Institute for Fundamental Sciences, Tabriz, Iran |
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Abstract: | The synthesis of various vinylbis(silanes) from some aryl and heteroaryl aldehydes and (Me3Si)3CLi in Et2O is described. Friedel-Crafts reaction of 1,1-bis(trimethylsilyl)-2-(2-naphthyl)ethene with various acyl chlorides (RCOCl, R = Me, Et, i-Pr, i-Bu, n-pent) gave the corresponding α-silyl-α,β-unsaturated enones with high E steroselectivity. Moreover, poly(styrene)-co-2,2-bis(trimethylsilyl)ethenyl(styrene)] obtained via the reaction of polymers bearing pendant enone functions and (Me3Si)3CLi, reacts with the same acyl chlorides in the presence of catalytic amount of AlCl3 to give the new macromolecules bearing α-silyl-α,β-unsaturated enones and α,β-unsaturated enones. |
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Keywords: | Tris(trimethylsilyl)methane Peterson olefination 1 1-Bis(silyl)-1-alkenes Functionalized poly(styrene) Friedel-Crafts reactions |
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