An Efficient Conversion of Carboxylic Acids to One-Carbon Degraded Aldehydesvia2-Hydroperoxy Acids | Zendy

Yoshihiko Akakabe | Zendy; Takeshi NYUUGAKU | Zendy

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An Efficient Conversion of Carboxylic Acids to One-Carbon Degraded Aldehydesvia2-Hydroperoxy Acids

Author(s) -

Yoshihiko Akakabe,

Takeshi NYUUGAKU

Publication year - 2007

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.70105

Subject(s) - lithium diisopropylamide , chemistry , aldehyde , carbon atom , carboxylic acid , carbon fibers , lithium (medication) , organic chemistry , ion , catalysis , materials science , ring (chemistry) , medicine , composite number , deprotonation , composite material , endocrinology

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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