Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 16, Pages 8028-8036Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo4013089
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- City University of New York
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Certain 2-aryl-3H-1-benzazepines are conformationally mobile on the NMR time scale. Variable-temperature NMR experiments bolstered by calculations indicate that alkylation of the azepine ring will slow the interconversion of conformational enantiomers markedly. DFT studies show that, while the substitution patterns of the aryl groups at C2 and C4 do not exert large effects on the rate of enantiomerization, alkylation at C5 slows it appreciably. Alkylation at C3 slows enantiomerization even more, possibly to the extent that isolation of atropisomers might be attempted.
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