Canadian Journal of Chemistry

Photochemical Syntheses: 6. The Formation of Heptandiones from Acetylacetone and Alkenes

P Mayo, H Takeshita

Index: de Mayo,P.; Takeshita,H. Canadian Journal of Chemistry, 1963 , vol. 41, p. 440 - 449

Full Text: HTML

Citation Number: 83

Abstract

The irradiation of acetylacetone in the presence of oct-1-ene, cyclopentene, cyclohexene, and 1-methylcyclohexene gives substituted heptandiones. These diketones may then be cyclized with acid or base. Irradiation of isopropenyl acetate and acetylacetone gives, after cyclization, m-5-xylenol. The mechanism of the reaction is discussed: it represents the first cycloaddition to an isolated ethylenic linkage.