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Alcoxide cleavage of benzoyl-t-butyl-diimide: carbanion and radical mechanisms

✍ Scribed by Gideon Fraenkel; Engelbert Pecchold

Book ID: 104240145
Publisher: Elsevier Science
Year: 1969
Tongue: French
Weight: 187 KB
Volume: 10
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)88819-5

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✦ Synopsis

Diimides or their conjugate bases have been proposed to be intermediates in the Wolff-Kishner reaction (1,2), the McFadyen-Stevens rearrangement (3), the hydrolysis of aryl-azoformate esters (4), the acid and base hydrolysis of benzoyl-phenyldiimide (5), the alcoxide cleavage of alkyl-benzoyldiimides (6), and the base cleavage of 1-aryl-2-tosyl-hydrazides ( 7).

The idea that it might be possible to generate carbanions from diimide anions, 1, is originally due to Cram (2) but so far if carbanions are intermediates in these reactions (l,T),

No.54

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