Rearrangements of organosilicon compounds using organoaluminum reagents. Conversion of phenyl- and alkenyl(chloromethyl)silanes to benzyl- and allylsilanes

Various (chloromethyl)silanes undergo Wagner-Meerwein-type rearrangements using a catalytic amount of EtAlCl 2 in dichloromethane. The resulting chlorosilanes have been converted to alkyl(or aryl)silanes with RMgX and/or to fluorosilanes with NH 4 HF 2 . In this way phenyl-, alkenyl-, and allyl(chloromethyl)silanes were converted to benzyl-, allyl-, and homoallylsilanes, respectively. Attempted rearrangements of methyl-, alkynyl-, and furyl(chloromethyl)silanes under these conditions were not successful