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A DNMR study on the ring inversion of oxazolidines
Author(s) -
Li Yang,
Kun Gao,
SuLing Kong,
YaoZu Chen
Publication year - 1990
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19900080508
Subject(s) - substituent , chemistry , oxazolidine , inversion (geology) , ring flip , linear correlation , polarity (international relations) , stereochemistry , computational chemistry , ring (chemistry) , crystallography , organic chemistry , structural basin , paleontology , biochemistry , statistics , mathematics , cell , biology
Ring inversion of eight substituted 2‐phenyl‐4, 4‐dimethyloxazolidines in o ‐dichlorobenzene‐ d 4 was studied by 1 H DNMR. Very high inversion barriers (Δ G o ≠ = 86.7–93.4 kJ·mol −1 ) were found for these oxazolidine rings. The magnitude of the inversion barrier is dependent on the polarity of the substituent on the phenyl group. A linear correlation is present between the Δ G o ≠ of the inversion and the substituent constant, σ+, of the substituent.
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