J. Bosch, A. Domingo, F. López
Mar 1, 1980
Citations
0
Influential Citations
5
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
1,3,3-Trimethyl-2-(3,4,5-trimethoxyphenyl)-4-methylenepiperidine (XI) is prepared in an unambiguous way which involves the Refortmatsky reaction followed by ethanolysis on the N-(3,4,5-trimethoxybenzylidene)methylamine, later treatment of the resulting aminoester with ethyl acrylate, ring closure by Dieckmann reaction with decarbalkoxylation and, finally, a Wittig reaction on the piperidone obtained. The resulting methylenepiperidine XI differs in its physical and spectroscopic data from the methylene derivative IIIa obtained by the Stevens rearrangement of the 1,3,4-trimethyl-1-(3,4,5-trimethoxybenzyl)-1,2,5,6-tetrahydropyridinium chloride, whose structure must be reviewed.