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Synthesis and epimerization of 1‐Alkyl‐2‐carbomethoxy‐4‐methyl (or phenyl)azetidines
Author(s) -
Kulkarni Shrikant B.,
Rodebaugh Richard M.,
Cromwell Norman H.
Publication year - 1976
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.5570130225
Subject(s) - chemistry , alkyl , epimer , aryl , medicinal chemistry , base (topology) , catalysis , deuterium , primary (astronomy) , hydrogen–deuterium exchange , organic chemistry , hydrogen , mathematical analysis , physics , mathematics , quantum mechanics , astronomy
A number of 1‐alkyl‐2‐carbomethoxyazetidines have been prepared from the reaction of primary amines with α,γ‐dibromoearbonyl compounds. A series of base catalyzed reactions performed on selected cis, trans ‐1‐alkyl‐2‐carbomethoxy‐4‐alkyl(aryl)azetidines reveal the cis isomer to be of greater thermodynamic stability. Furthermore, base catalyzed deuterium exchange studies suggest this to be the case.