1968 Volume 41 Issue 5 Pages 1170-1174
The nature of intramolecular hydrogen bonding in diastereoisomeric pairs of 10-nor-8-oxomenthols (VIII and IX) and 10-nor-8-oxocarvomenthols (X and XI) has been studied by infrared spectroscopy. It was found that 10-nor-8-oxoneomenthol (IX) contains the OH···O type intramolecular hydrogen bond, while 10-nor-8-oxomenthol (VIII) contains the OH···π interaction in addition to the OH···O hydrogen bond. 10-Nor-8-oxocarvomenthols (X and XI) were internally unbonded. In addition, the extent and the limitation of the intramolecular OH···π interaction has been investigated for the diastereoisomeric pairs of a series of p-menth-8-enols: p-menth-8-en-4-ols (I and II), isopulegols (III and IV), dihydrocarveols (V and VI), and trans-β-terpineol (VII). Thus, the hydroxyl group in α- or β-unsaturated alcohols I, II, III and IV was found to be internally bonded to the π-electrons on the double bond; the other isomers are internally unbonded.
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