(1R,2S,4r)-1,2,4-Triphenylcyclopentane-1,2-diol and (1R,2S,4r)-4-(2-methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol: application as initiators for ring-opening polymerization of ∊-caprolactone

Abstract

Reductive cyclization of 1,3,5-triphenyl- and 3-(2-methoxyphenyl)-1,5-diphenylpentane-1,5-diones by zinc in acetic acid medium leads to the formation of 1,2,4-triphenylcyclopentane-1,2-diol [1,2,4-Ph3C5H5-1,2-(OH)2, C23H22O2, (I)] and 4-(2-methoxyphenyl)-1,2-diphenylcyclopentane-1,2-diol [4-(2-MeOC6H4)-1,2-Ph2C5H5-1,2-(OH)2, C24H24O3, (II)]. Their single crystals have been obtained by crystallization from a THF/hexane solvent mixture. Diols (I) and (II) crystallize in orthorhombic (Pbca) and triclinic (P\overline{1}) space groups, respectively, at 150 K. Their asymmetric units comprise one [in the case of (I)] and three [in the case of (II)] crystallographically independent molecules of the achiral (1R,2S,4r)-diol isomer. Each hydroxyl group is involved in one intramolecular and one intermolecular O—H...O hydrogen bond, forming one-dimensional chains. Compounds (I) and (II) have been used successfully as precatalyst activators for the ring-opening polymerization of ∊-caprolactone.