Abstract
Phenyl(trihalomethyl)mercury compounds react with highly halogenated ketones [(CF 3) 2CO, CF 3COCF 2Cl, (CF 2Cl) 2CO, CF 2ClCOCFCl 2], aldehydes (n-C 3F 7CHO, CCl 3CHO) and acid chlorides (CF 3COCl, CCl 3COCl) to add CX 2 to the CO bond, giving oxiranes. In the case of hexachloroacetone and n-C 3F 7OCF(CF 3)CF 2OCF(CF 3)C(O)F, ketones were obtained instead. In the reactions with the acid chlorides, ketones also were formed in addition to the oxiranes. Reaction of PhHgCCl 2Br with oxalyl chloride produced the expected oxirane, 2,3,3-trichloro-2,3-epoxypropenoyl chloride, as well as trichloropyruvyl chloride, trichloroacetyl chloride and hexachlorobiacetyl. A reaction of this mercury reagent with benzil gave PhC(O)-CClPh-C(O)(Cl, most likely via rearrangement of the initially formed oxirane.
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