4-Formyl-2-cyclohexenone Derivatives

Abstract

Recent interest in γ-alkylation of α,β-unsaturated carbonyl compounds¹ has focused on the possibility of α'-alkylation of β-alkoxy α,β-unsaturated keto systems,² e.g. 1, hydride reduction of the products and acid-catalyzed hydrolysis of the resultant alkoxyallyl alcohols.³ Quite some time earlier the α' carbon had been shown to be the site of acylation of a β-alkoxy α,β-unsaturated ketone, i.e. 1 → 2 on formylation.⁴ Since a reduction-hydrolysis reaction sequence on the O-protected derivative 3 ^4b might lead to 4-formyl-2-cyclohexenone (or its equivalent), a trifunctional substance of potential interest in organic synthesis, some of the chemistry of ketones 2 and 3 was investigated.