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The synthesis of l‐alkyl‐2‐benzoyl‐4‐methylazetidine. Configurational and conformational studies
Author(s) -
Kulkarni Shrikant B.,
Cromwell Norman H.
Publication year - 1977
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.5570140606
Subject(s) - chemistry , alkyl , yield (engineering) , base (topology) , primary (astronomy) , deuterium , medicinal chemistry , hydrogen–deuterium exchange , catalysis , organic chemistry , thermodynamics , mathematical analysis , physics , mathematics , quantum mechanics , astronomy , hydrogen
α,γ‐Dibromovalerophenone ( 3 ) reacted with primary amines to give a number of l‐alkyl‐2‐benzoyl‐4‐methylazetidines ( 4 ) in good yield. The results of the base catalyzed reactions performed on these new carboazetidines imply that the cis isomer is of greater thermodynamic stability. Furthermore, base catalyzed deuterium exchange studies suggest this to be the case. J. Heterocyclic Chem. , 14, 981 (1977)