The kinetics of regioselective dichlorocyclopropanation of 4-vinyl-1-cyclohexene has been studied under controlled phase transfer catalysis conditions, using aqueous sodium hydroxide as the base and 2-benzylidine-N,N,N,N',N',N'-hexaethylpropane-1,3-diammonium dibromide (Dq-Br) as a new phase transfer reagent, The reaction was carried out at 40 degrees C under pseudo-first order conditions by employing aqueous sodium hydroxide and chloroform in excess and was monitored by gas chromatography. The effect of various experimental parameters on the rate of the reaction has been studied and based on the experimental results, a suitable mechanism is proposed.