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

Article abstract of DOI:10.1246/bcsj.54.2053

A selsctive attack of dichlorocarbene at the para-position of the phenolate has been achieved by using α-cyclodextrin 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 (82percent) is dominant over the attack at the ortho-position (18percent) in the presence of 0.15 mol dm^-3 of α-cyclodextrin, which is in contrast with the predominance of the ortho-attack (59percent) over the para-attack (41percent) in the absence of α-cyclodextrin.