Electrolytic Decarboxylation. 6. A Convenient Synthesis of 3-(cis-3-Hexenyl)-2-cyclopentenone, a Precursor of cis-Jasmone Synthesis

DOI: 10.1246/bcsj.55.3947

Source and publish data:

Bulletin of the Chemical Society of Japan p. 3947 - 3948 (1982)

Update date:2022-07-30

Topics:

Authors:

Torii, Sigeru

Tanaka, Hideo

Inokuchi, Tsutomu

Tomozane, Kazuo

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Article abstract of DOI:10.1246/bcsj.55.3947

A regioselective electro-acetoxylation of 1-(cis-3-hexenyl)-2-cyclopentene-1-carboxylic acid in a Et3N-AcOH-AcOEt-t-BuOH-(Pt electrodes) system afforded 3-acetoxy-1-(cis-3-hexenyl)-1-cyclopentene (7a) (98percent).Alkaline hydrolysis of 7a followed by the oxidation with chromium trioxide gave the desired 3-(cis-3-hexenyl)-2-cyclopentenone smoothly.

Full text of DOI:10.1246/bcsj.55.3947

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