[1631-83-0] · C12H11ClSi · Chlorodiphenylsilane · (MW 218.76)
Physical Data: bp 140-145 °C/7 mmHg (99-101 °C/1 mmHg; 83-85 °C/0.4 mmHg); d 1.137 g cm-3; n 1.5845.
Solubility: sol benzene, chloroform, carbon tetrachloride, and ether.
Form Supplied in: liquid. Commercially available.
Handling, Storage, and Precautions: moisture sensitive. Reactions are typically conducted under an inert atmosphere. The compound is corrosive and liberates HCl upon contact with moisture; may burn exposed skin and can be destructive to eyes, mucous membranes, and upper respiratory tract. Chemically incompatible with water, alcohols, and amines.
In the presence of a catalyst (typically chloroplatinic acid, H2PtCl2), chlorodiphenylsilane hydrosilylates double and triple bonds. As a difunctional reagent, chlorodiphenylsilane may be used in a reaction with an organometallic reagent (see the following section) to displace chlorine prior to the hydrosilylation reaction as in eq 15 or hydrosilylation may be conducted first with subsequent reaction at silicon as illustrated in eq 2.6 The regiochemistry of the reaction has been reviewed.7
An enantioselective synthesis of chiral diols via intramolecular hydrosilylation using a chiral catalyst followed by oxidative cleavage of the Si-C bond (with retention of configuration) has been reported.8 Intramolecular hydrosilylation/oxidation of Triethylsilane.
Dallas K. Bates Michigan Technological University, Houghton, MI, USA
Chloride Displacement by Organometallic Reagents.
Copyright © 1995-2000 by John Wiley & Sons, Ltd. All rights reserved.
Dallas K. Bates
Michigan Technological University, Houghton, MI, USA