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A reinvestigation of the stevens rearrangement of 1,3,4‐trimethyl‐1‐(3,4,5‐trimethoxybenzyl)‐1,2,5,6‐tetrahydropyridinium chloride
Author(s) -
Bosch J.,
Domingo A.,
Lopez F.,
Rubiralta M.
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170207
Subject(s) - chemistry , methylene , derivative (finance) , chloride , methylamine , medicinal chemistry , rearrangement reaction , acrylate , ring (chemistry) , wittig reaction , organic chemistry , catalysis , polymer , monomer , financial economics , economics
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.