Dichlorocarbene from Flash Vacuum Pyrolysis of Trimethyl(trichloromethyl)silane. Possible Observation of 1,1-Dichloro-3-Phenyl Carbonyl Ylide

Article abstract of DOI:10.1021/jo00212a009

Flash vacuum pyrolysis of trimethyl(trichloromethyl)silane 3 at 500-700 deg C was shown to be a simple and efficient method for the production of :CCl2 in the gas phase.The copyrolysis of silane 3 and benzaldehyde (7) at 600 deg C led to 1,1,1-trichloro-2-phenyl-2-(trimethylsiloxy)ethane (8), a 1:1 adduct, in addition to benzal chloride (15) and α-chlorophenylacetyl chloride (16), product thought to arise from 1,1-dichloro-3-phenyl carbonyl ylide 17 as outlined in Scheme I.An orange-red material trapped at deg K could be photobleached as well as thermally bleached and had an IR band at 1650 cm^-1 and a si gnificant absorption with λ_max 510 nm (and a broad shoulder at a 580 nm).