Specific Catalysis by α-Cyclodextrin on the Dichlorocarbene Attack at Phenolate

A selective attack of dichlorocarbene at the para-position of phenolate has been achieved by using α-cyclo-dextrin and the reaction mechanism has been studied by the 13C-NMR and 1H-NMR spectroscopy. The attack of the carbene at the para-position of phenolate (82%) is dominant over the attack at the ortho-position (18%) in the presence of 0.15 mol dm−3 of α-cyclodextrin, which is in contrast with the predominance of the ortho-attack (59%) over the para-attack (41%) in the absence of α-cyclodextrin.