脂肪族カルボン酸エステル,酸無水物,酸クロリドなどとビニルマグネシウムクロリドの反応

概要

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Reaction of vinylmagnesium chloride with aliphatic carboxylic acid methyl ester gives a mixture of vinylketone and divinylcarbinol. From methyl pentanoate, a mixture of n-butyl-3-hydroxyl-1, 4-pentadiene and 5-oxo-1-nonene is obtained. While reaction of linear α, β-unsaturated methyl esters with vinylmagnesium chloride yields vinylketones as the main product, the reaction of substituted α, β-unsaturated methyl esters yields triethylenic carbinols. Reaction of acid anhydrides and dibasic acid diesters with vinylmagnesium chloride yields mixtures of alkenones, hydroxy-alkenones and alkenols as the main products. Reaction of acid chloride with excess vinylmagnesium chloride at -40°C to -45°C gives 2-allyl-1, 3-diketones. From propanoyl chloride, a mixture of 4-allylheptane-3, 5-dione (33% yield), 6-heptene-3-one (0.5% yield) and 3-ethyl-1, 4-pentadiene-3-ol (2% yield) is obtained. Reaction of vinylmagnesium chloride with a fatty acid methyl ester in the presence of cuprous chloride gives a 1, 6-diketone. From methyl n-valerate, a mixture of n-tetradecane-5, l0-dione and 5-oxo-1-nonene is obtained.
日本油化学会の論文