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Steric controls in the preparation of 1‐benzyl‐1,4‐dihydro‐3‐(2 H )isoquinolones and 1‐benzyl‐1,2,4,5‐tetrahydro(3 H )‐2‐benzazepin‐3‐ones via Beckmann rearrangement
Author(s) -
Jensen Bruce L.,
Michaud Dennis P.
Publication year - 1978
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.5570150230
Subject(s) - chemistry , steric effects , beckmann rearrangement , stereochemistry , medicinal chemistry , oxime
The effect of substituents in the 1‐position of 2‐indanones and 2‐tetralones on the course of Beckmann rearrangement reactions was studied. Nmr spectral anaylses of the intermediate oximes and final products demonstrated that steric controls were operative both before and during rearrangement. Use of the appropriate substituents and reaction conditions makes this reaction scheme attractive for preparation of the title compounds.