Syntheses and chemistry of some dibenz[c,e]azepines
5-Methyl-,5,7-dimethyl-, and 5,7-diphenyl-substituted and unsubstituted 5H-dibenz[c,e]azepines were prepared by two general routes from [1,1''-biphenyl]-2,2''-dicarboxaldehyde. The unsubstituted dibenzazepine was converted into la,9b-dihydrophenanthro[9,10-b]azirine both by lithi...
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Published in | Journal of organic chemistry Vol. 52; no. 4; pp. 529 - 536 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
01.02.1987
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | 5-Methyl-,5,7-dimethyl-, and 5,7-diphenyl-substituted and unsubstituted 5H-dibenz[c,e]azepines were prepared by two general routes from [1,1''-biphenyl]-2,2''-dicarboxaldehyde. The unsubstituted dibenzazepine was converted into la,9b-dihydrophenanthro[9,10-b]azirine both by lithium diisopropylamide (LDA) and by UV irradiation. The disubstituted azepine derivatives failed, however, to undergo valence isomerization under such conditions. N-Benzylphenanthrene 9,10-imine was obtained directly from 2''-(bromomethyl)[1,1''-biphenyl]-2-carboxaldehyde and excess benzylamine. Aerial oxidation of 5,7-diphenyldibenz[c,e]azepine in the presence of 50% aqueous NaOH led, under phase-transfer conditions, to 5,7-diphenyldibenz[c,e]azepin-5-ol. Special structural features of this carbinol found by X-ray analysis are discussed. |
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Bibliography: | ark:/67375/TPS-7W96DH0M-5 istex:36451694A950AE2F622089974B71889D8EE8EE18 |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo00380a010 |