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Evidence for rate limiting C-H bond cleavage in the leuckart reaction

✍ Scribed by Peter I. Awachie; Vincent C. Agwada

Book ID
104204918
Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
772 KB
Volume
46
Category
Article
ISSN
0040-4020

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✦ Synopsis

A rho value of +0.21 is reported for the reaction of mono 4-substitutad benzophenoneswith formamide. This, in conjunction with a kinetic isotope effect value of 1.80 obtained for the system, suggests a rate-limiting C-H bond cleavage.

The Leuckart reaction, a process for the alkylation of ammonia or amines or their formyl derivatives by aldehydes or ketones, is a facile route to a

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## Abstract Recent theoretical studies of the alkaline hydrolysis of the amide bond have indicated that the nucleophilic attack of the hydroxide ion at the carbonyl carbon of the amide group is rate limiting. This is shown to be inconsistent with a large amount of experimental observations where th