Collect. Czech. Chem. Commun.
1985, 50, 956-961
https://doi.org/10.1135/cccc19850956
Evolution thermique de N-oxydes de dimethylamino-5 alcanols-1 substitues en 5. Competition entre rearrangements de cope et de Meisenheimer
Didier Barbry, Bruno Hasiak, Jean-Michel Augait and Daniel Couturier
Laboratoire de Synthèse Organique - C4, Université des Sciences et Techniques de Lille, 59655 Villeneuve d'Ascq Cédex, France
Abstract
The effect of the substituent R in the position was studied in the decomposition of 1,5-aminoalcohol N-oxides: Meisenheimer rearrangement takes place when R is the vinyl group but is not observed with the phenyl substituent; elimination to alkenol only affects the more acidic hydrogen atom when R is the allyl or benzyl group; with substituents inducing less important electronic effects (methyl, ethyl), the reaction yields an alkenols mixture with statistical distribution.
