Reaction of Phosphorus Pentachloride with 4-Methyl-1,1,1-trichloro-4-penten-2-ol

摘要

Phosphorylation of alkenols with phosphorus pentachloride has not been studied so far.We first studied behavior in this reaction of 4-mefhyl-1,1,1-trichloro-4-pentene-2-ol(I),an intermediate in the industrial synthesis of a piretroid preparation permetrin.The process was carried out using an inert organic solvent(benzene,carbon tetrachloride or toluene)under mild conditions(0-5°C).We found that at equimolar reagent ratio occurs O-phosphorylation of alcohol I.By the data of IR spectroscopy and ~1H and ~(31)P NMR spectroscopy,the reaction product is 4-methyl-1,1,1- trichloropent-4-en-2-yl dichlorophosphate(II)(8p 10 ppm).