Generation of phenylcarbenes and ethoxycarbonylnitrene from alpha-(leaving group)-substituted organosilanes
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A method for the generation of phenylcarbenes and ethoxycar- bonylnitrene through fluoride ion-induced alpha-elimination of alpha-(leaving group)-substituted organosilanes was studied. The precursors used for the generation of phenylcarbenes were trimethyl ( dlchlorophenylmethyl)silane and trimethyl(diphenylchloromethyl)- silane, and those for ethoxycarbonylnitrene generation were N-trimethylsilyl-N-chlorourethane and N-trimethylsilyl-N-(p-nitro- benzenesulfonoxy)urethane. The reaction of trimethyl(dichlorophenyl- methyl)silane with potassium fluoride transferred phenylchlorocarbene to olefins in good yield at room temperature. Trimethyl(diphenylchlorome thyl) silane failed to transfer diphenylcarbene under similar conditions. No aziridines were obtained from attempts to transfer ethoxycarbonylnitrene to cyclohexene from the nitrene precursors listed above.