Abstract
The stereochemistry of allylic oxidation of trans-β-terpinyl acetate (1) and cis-β-terpinyl acetate (2) by selenium dioxide were studied. In each case, both the methine group at C4 and the methyl group at C9 of (1) and (2) were oxidized, and the reactivity sequence was CH>CH3. The trans- and cis-8-p-menthene-1-acetoxy-4-ols ((1c) and (1d)) were obtained by the oxidation of (1) and (2), respectively. The acetoxy group at C1, has no steric hindrance toward the oxidation of the methine group at C4, and so there is little stereoselectivity observed in the tertiary alcohols (1c) and (1d). The reaction path of the oxidation of (1) and (2) was also elucidated by Bhalerao's mechanism described in the previous papers.
