Abstract
Reactions of phosphorus pentachloride with ethyl(trichloromethyl)carbinol (2), (trichloromethyl)-vinylcarbinol (7), ethynyl(trichloromethyl)carbinol (11a), and 1,1,1-trichloro-3-nonyn-2-ol (11b) have been studied. Whereas the reaction of phenyl(trichloromethyl)carbinol with phosphorus pentachloride leads to a nearly quantitative replacement of the hydroxyl group by chlorine, the reactions of the aliphatic (trichloromethyl)carbinols are more complicated. Thus the reaction of 2 with phosphorus pentachloride gave 18% of the normal product, 1,1,1,2-tetrachlorobutane (3), 13% of 1,1,2-trichloro-1-butene (4) from a dehydrohalogenation, and a higher boiling phosphate ester – acid chloride mixture. The alkynylcarbinols (11) gave tetrachlorobutynes (12) as well as tetrachloroallenes (13) by allylic rearrangement. A crystalline phosphate ester of 11a was also isolated. Several examples are given of catalytic rearrangements in the vapor phase of 1,1,1-trichloro-2-alkenes to 1,1,3-trichloro-1-alkenes.
Published Version
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