The Reaction of Fatty Acid Esters, Acid Anhydride, and Acid Chloride with Vinylmagnesium Chloride

DOI Web Site Web Site Open Access
  • WATANABE Shoji
    Department of Applied Chemistry, Faculty of Engineering, Chiba University
  • SUGA Kyoichi
    Department of Applied Chemistry, Faculty of Engineering, Chiba University
  • FUJITA Tsutomu
    Department of Applied Chemistry, Faculty of Engineering, Chiba University
  • TAKAHASHI Yukio
    Department of Applied Chemistry, Faculty of Engineering, Chiba University
  • KOISO Hideyuki
    Department of Applied Chemistry, Faculty of Engineering, Chiba University

Bibliographic Information

Other Title
  • 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
  • シボウゾク カルボンサン エステル , サン ムスイブツ , サン クロリド ナド ト ビニル マグネシウム クロリド ノ ハンノウ

Search this article

Description

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.

Journal

Details 詳細情報について

Report a problem

Back to top