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

✍ Scribed by S. H. Harper; K. C. Sleep

Publisher
John Wiley and Sons
Year
1955
Tongue
English
Weight
421 KB
Volume
6
Category
Article
ISSN
0022-5142

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✦ Synopsis

Abstract

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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