Cycloalkylation of phenylacetonitrile with 1,4-dibromobutane catalyzed by aqueous sodium hydroxide and a new phase transfer reagent, Dq-Br Original Research Article

The kinetics of cycloalkylation of phenylacetonitrile (PAN) with an excess of 1,4-dibromobutane has been studied under phase transfer catalysis (PTC) conditions using aqueous sodium hydroxide as the base and 2-benzilidine-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 70°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; based on the experimental results, a suitable mechanism is proposed.