The effect of substituents on the helical twisting power of aldol condensation products of menthone

Abstract

The helical twisting powers of the E-isomers of aldol condensation products of menthone and aromatic aldehydes are higher than those of the Z-isomers. In order to find out which chiral centre of these menthone derivatives is responsible for the value of the helical twisting in both isomers, the E-isomers of aldol condensation products of 3-methylcyclohexanone and 2-isopropylcyclohexanone were prepared and photoisomerized to form Z-isomers. The physical properties of these species were determined. It was concluded that the strong helical twisting power of the E-isomers of the derivatives of menthone is caused by the chiral carbon atom containing the methyl group in the ring. The relatively low helical twisting power of the Z-isomers and the composition of the E-Z isomers in the photostationary state are determined mainly by the other chiral centre containing the isopropyl group.