An efficient conversion of carboxylic acids to one-carbon degraded aldehydes via 2-hydroperoxy acids |
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Authors: | Akakabe Yoshihiko Nyuugaku Takeshi |
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Institution: | Department of Biological Chemistry, Faculty of Agriculture, Yamaguchi University, Yamaguchi, Japan. akakabe@yamaguchi-u.ac.jp |
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Abstract: | After the formation of dianions of a carboxylic acid with lithium diisopropylamide, oxygen was bubbled into the solution to produce 2-hydroperoxy acid. Then the reaction mixture was acidified with a 2 N HCl solution and subsequently elevated to 50 degrees C to afford the aldehyde with the loss of one carbon atom. Even saturated (C(10)-C(20)) and unsaturated (C(18:1)) carboxylic acids were converted into the odd aldehydes (C(9)-C(19), C(17:1)) in high yields. This conversion was found to be an efficient method for the preparation of carboxylic acids (Cn) to one-carbon degraded aldehydes (Cn-1) via 2-hydroperoxy acids. |
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