Premium
Réaction d'énamines dérivées de la cyclohexanone avec le tétracyanoéthylène
Author(s) -
Hubschwerlen Christian,
Fleury JeanPierre,
Fritz Hans
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600811
Subject(s) - chemistry , tetracyanoethylene , cyclohexanone , enamine , reactivity (psychology) , medicinal chemistry , zwitterion , nitrile , stereochemistry , photochemistry , organic chemistry , catalysis , molecule , medicine , alternative medicine , pathology
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.