Saturated heterocycle-condensed diphenylisoindolones: Fused-skeleton tetrahydro-1,3-oxazines, oxazolidines and imidazolidines

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Abstract

The addition of benzene to cis-4-cyclohexene-1,2-dicarboxylic anhydride yielded c-2-benzoyl-t-5-phenyl-r-1-cyclohexanecarboxylic acid (72%), or in another reaction, the 4-phenyl isomer (67%). With bifunctional reagents, saturated tricyclic or partially saturated tetra- and pentacyclic hetero derivatives containing an isoindolone moiety were prepared. The cis → trans isomerization in the ring closures is promoted by enolization and by the two close-lying phenyl groups. The stereostructures of the products were determined via 1H and 13C NMR spectroscopy.

Original languageEnglish
Pages (from-to)187-195
Number of pages9
JournalJournal of Molecular Structure
Volume382
Issue number3
DOIs
Publication statusPublished - Nov 27 1996

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Keywords

  • Configurational isomerism
  • Diphenyl isoindolone
  • NMR spectroscopy

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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