Abstract
Acetylation of the angular OH in (IVα) and (IVβ) was attempted and respective monoacetylated compounds (VIIα and VIIβ) were produced. It was found that, similar to the dehydration and chlorination reactions reported in the preceding paper, the α-type reacted more easily than β-type in this reaction. Catalytic reduction of (IVα) and (IVβ) resulted in absorption of 1 mole of hydrogen in each case to afford (IXα) and (IXβ). The same difference between the two isomers was also found in this case, β-type requiring ca. 5 times longer than α-type in absorption of 1 mole of hydrogen. The difference in the reactivity of hydroxyl and carbonyl between α- and β-types is considered to be due to their steric configuration. It was found through the present series of experiments that (IVα) and (IVβ) possessed one hydroxyl and one carbonyl groups in each molecule and that the isomerization does not occur by their acetylation and reduction.
