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New PDF release: Advances in Organometallic Chemistry 53

By Robert West (ed.), Anthony F. Hill (ed.), F. Gordon A. Stone (ed.)

ISBN-10: 0120311534

ISBN-13: 9780120311538

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V. Hydrosilylation Reaction with Triorganosilanes . . . . . . . . Acknowledgments . . . . . . . . . . . . . . . . . . References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41 42 42 48 49 50 50 53 55 56 57 58 58 I INTRODUCTION This review will describe Lewis acid-catalyzed reactions such as allylsilylation, intramolecular allyl-migration, Friedel–Crafts alkylation, and hydrosilylation reactions commonly used in organosilicon chemistry.

Under the same reaction conditions, trans-1-allyl-2(trimethylsilyl)cycloalkenes are isomerized to 3-[3-(trimethylsilyl)propyl]cycloalkenes. Thus, both starting trans-1-allyl-2-(trimethylsilyl)cyclopentene and -hexene are isomerized to 3-(3-(trimethylsilyl)propyl)cyclopentene (24%) and 3-(3(trimethylsilyl)propyl)cyclohexene (15%), respectively [Eq. (7)]. It seems reasonable that the first step in the isomerization is the addition of a silyl cation to the carbon– carbon double bond of the trans-1-allyl-2-(trimethylsilyl)cycloalkanes followed by a 1,5-hydride shift to give a carbocation on a ring carbon b to the silyl group.

N. R. YOO or more chlorine substituents on silicon react readily with aromatic compounds to give alkylation products, 2-aryl-1-silylpropanes [Eq. 3 However, allyltrimethylsilane, having three methyl groups on the silicon (1a), in benzene solvent is dimerized to give the allylsilylation product 5-(trimethylsilyl)-4-(trimethylsilylmethyl)-1-pentene without any alkylation products [Eq. 1b,2 This facilitates the protodesilylation1a,2,10 of allyltrimethylsilane by hydrogen chloride in the presence of aluminum chloride, which gives propene and a Me3SiCl–AlCl3 complex.

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Advances in Organometallic Chemistry 53 by Robert West (ed.), Anthony F. Hill (ed.), F. Gordon A. Stone (ed.)


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