Chemical Properties
Colorless to Almost colorless clear liquid.
Uses
Diethyl (trichloromethyl)phosphonate may be used in the synthesis of chlorovinyl phosphonates via reaction with aldehydes and ketones.
Preparation
Diethyl trichloromethylphosphonate was also obtained from diethyltrimethylsilyl phosphite in 60 % yield, and from benzyldiethyl phosphite in the presence of dibenzoyl peroxide and an ultraviolet source in a radical induced reaction in 87 % yield (compared to 26 % without the dibenzoyl peroxide).
Application
Diethyl trichloromethylphosphonate has been used as a carbenoid precursor in the reaction with Bu3B.
Diethyl trichloromethylphosphonate is used mainly in the synthesis of 1,1-dichloro-1-alkenes from carbonyl compounds via Horner–Wadsworth–Emmons (HWE)-type reactions.
Diethyl trichloromethylphosphonate reacts with olefins under Cu(I) or Fe(III) catalysis to give insertion of the olefinic substrate into one of the C–Cl bonds.
General Description
Addition reaction of diethyl (trichloromethyl)phosphonate to olefins by non-chain catalytic reactions catalyzed by copper amine complexes has been reported. Irradiation of diethyl (trichloromethyl)phosphonate
in MeCN is reported to afford corresponding monoesters and olefins,
via photochemical type II elimination reaction.
