Carbene chemistry. Part IX. Some C-H insertion reactions of dichlorocarbene in the gas phase
Abstract
Dichlorocarbene, from the thermal decomposition of trifluoro(trichloromethyl)silane at 140–180 °C in the gas phase, gives good yields of α-C–H insertion products with ethylbenzene, cumene, diethyl ether, 2-methoxypropane, and tetrahydrofuran. The tertiary C–H bond of isobutane is 70 times more reactive than a C–H bond of cyclohexane at 140 °C, and no products of insertion into primary C–H bonds have been identified with certainty. Dichlorocarbene reacts with cyclopentadiene at 180 °C to give chlorobenzene (58 %) and with indene to give 2-chloronaphthalene (69 %).