アルデヒドとα,β-不飽和ケトンとのラジカル付加反応によるジャスモン類の合成

概要

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Radical addition reactions of aldehydes to α,β-unsaturated ketones were carried out to give 1,4-diketones, which are key intermediates for jasmones, under an inert atmosphere at 90-95℃ with benzoyl peroxide. The addition of heptyl aldehyde [4a] to methyl vinyl ketone [5] yielded 2,5-undecadione [6a] in 10% yield. The by-products in this reaction were, identified as heptoic acid [12] and 2,4,6-trihexyl-1,3,5-trioxane [13]. By the radical addition of acetaldehyde [11] to hexyl vinyl ketone [10], 2,5-undecadione [6a] was obtained in 20% yield. Similarly, cis-4-heptenyl aldehyde [4b] was added to methyl vinyl ketone [5] and cis-8-undecen-2,5-dione [6b] was obtained in about 10% yield. The by-products were determined as 2-(2'-pentenyl)-2,6-nonadienal [14] and 4-propyl-8-undecen-5-one-1-al [15] (or 5-ethyl-9-dodecen-6-one-1-al [16]).
明治大学の論文