Abstract
Hydroxyl stretching bands have been recorded for some 3-cyclohexen-1-ols and 1-alky1-3-cyclo-hexen-1-ols in dilute carbon tetrachloride solutions. The 3-cyclohexen-1-ols [1] - [3 ] showed two peaks at 3612-3615 and 3623-3628 cm-1. In the case of the alcohols with adjacent isopro-pyl group, however, both the trans [ 4 ] and cis isomers [ 5] showed three peaks, each at 3612, 3623, and 3634 cm-1; 3601, 3623, and 3634 cm-1, respectively. On the other hand, 1- alkyl-3-cyclohexen-1-ols [ 6 ]-[10] showed two peaks at 3599-3603 and 3616-3619 cm-1 except for the (E)-1, 3-dimethyl-6-isopropyl-3-cyclohexen-1-ol [11] which had two peaks at 3615 and 3624 cm-1. These compounds are concluded to be present mainly in half-chair conformation. The con-formation with the equatorial substituent in the homoallylic position is more stable than the conformation with the axial substituent. When the hydroxyl group is forced to exist in the axial position, it interacts intramolecularly with π -electrons of double bond.
