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Réaction d'énamines dérivées de la cyclohexanone avec le tétracyanoéthylène

✍ Scribed by Christian Hubschwerlen; Jean-Pierre Fleury; Hans Fritz

Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
455 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis

Reaction with Tetracyanoethylene of Enamines derived from Cyclohexanone

At room temperature enamines of cyclohexanone react with tetracyanoethylene (TCNE) to give substituted tetrahydroindenes 5. The structures are assigned on the basis of ^13^C‐NMR. data and confirmed by hydrolysis. Spectroscopic studies (IR., UV., ESR.) at different temperatures indicate that the reaction can follow two routes: classical zwitterion formation, or a concurrent electron transfer between the enamines and TCNE leading to the derivates 5. These are the first reported examples of the γ‐carbon reactivity of an enamine.

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