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A new enamine reaction: synthesis of 3-amino-1,2-diazetidines

✍ Scribed by L. Marchetti; G. Tosi

Publisher: Elsevier Science
Year: 1971
Tongue: French
Weight: 215 KB
Volume: 12
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)97093-5

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✦ Synopsis

Cyclohexanone enamines react with dibenzoyldiimide (IIa) at room temperature leading to a I:1 addition product in almost quantitative yield. This adduct, on mild acidic hydrolysis, gives 2-(N,N'-dibenzoyl)hydrazinccyclohexanone (IVa), identical with that obtained from cyclohexanone and (IIa) at lOOa, in the presence of sulphuric acid.

Four structures, (III), (V), (VI) and (VII) could be postulated for the I:1 adduct. The formation of these compounds should be analogous to that of cyclobutane derivatives (1,2), substituted enamines (3) and heterocyclic adducts (4) from the same enamines with electrophilic alkenes, ethyl azodicarboxylate (5) and a, S-unsaturated ketones, respectively.

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