Abstract
Conditions for the direct and indirect side-chain oxidation of methylnaphthalenes were explored, together with substituent effects likely to influence the acidity of their radical-cations. That substituent effects alter the electron demand at side-chain positions was shown using chemical shifts (13C) at the benzylic carbons of 2-benzylnaphthalenes substituted at the para position of the benzyl group. However, the reactivity of 2-methylnaphthalenes in direct anodic oxidation ranges from exclusive dimerisation to exclusive nuclear substitution with negligible attack at the methyl group.
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