The chrysanthemumcarboxylic acids. VIII.  —A modified route to the chrysanthemic acids | Zendy

Harper S. H. | Zendy; Sleep K. C. | Zendy

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The chrysanthemumcarboxylic acids. VIII. —A modified route to the chrysanthemic acids

Author(s) -

Harper S. H.,

Sleep K. C.

Publication year - 1955

Publication title -

journal of the science of food and agriculture

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.782

H-Index - 142

eISSN - 1097-0010

pISSN - 0022-5142

DOI - 10.1002/jsfa.2740060210

Subject(s) - hydrolysis , chemistry , adduct , epimer , nitrile , alkaline hydrolysis , cis–trans isomerism , organic chemistry

Diazoacetonitrile is prepared in one stage from methyleneaminoacetonitrile and added to 2 : 5‐dimethylhexa‐2 : 4‐diene. The resultant mixture of (±)‐ trans ‐ and (±)‐ cis ‐chrysanthemonitrile is hydrolysed to (±)‐ trans ‐chrysanthemamide and to (±)‐ trans ‐chrysanthemic acid. It is shown that (±)‐ cis ‐chrysanthemonitrile undergoes conversion into the trans ‐isomer (epimerization) during alkaline hydrolysis. Hence the adduct nitrile hydrolyses to chrysanthemic acid containing no more than a trace of the cis ‐isomer.

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