Synthesis and Diels-Alder reactions of (E)-6, 6-dimethoxy-3-hexen-2-one

P Yates, SP Douglas

Index: Yates, Peter; Douglas, Stephen Paul Canadian Journal of Chemistry, 1982 , vol. 60, p. 2760 - 2765

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Citation Number: 8

Abstract

Treatment of 3, 3-dimethoxypropanal (2) with (acetylmethylene) triphenylphosphorane (4) gives (E)-6, 6-dimethoxy-3-hexen-2-one (5). Reaction of 5 with cyclopentadiene, 1, 3- cyclohexadiene, anthracene, and 1, 3-diphenylisobenzofuran gives Diels-Alder adducts, which on hydrolysis are converted to the corresponding keto aldehydes. Attempts to effect intramolecular aldol condensation of the latter were unsuccessful. Hydrolysis of the exo- ...