Separation and Identification of Residual Diastereomers in a Maximally Labeled Triarylamine

Robert Glaser, John F. Blount, Kurt Mislow

Research output: Contribution to journalArticlepeer-review

59 Scopus citations


Residual diastereoisomerism in a maximally labeled triarylamine, methyl N-(biphenyl-2-yl)-N-(l-naphthyl)anthranilate, has been demonstrated for the first time. The two stereoisomers were obtained by manual separation of crystals, and their structures were determined by X-ray analysis. Both isomers are molecular propellers, with the three ortho substituents on the triphenylamine skeleton pointing toward the apex of the nitrogen pyramid. Interconversion of the residual diastereomers requires ∆G± = 17.8 kcal/mol. It is noted that the central nitrogen atom in these systems is a nonstereogenic chiral center.

Original languageEnglish
Pages (from-to)2777-2786
Number of pages10
JournalJournal of the American Chemical Society
Issue number8
StatePublished - 1 Jan 1980
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


Dive into the research topics of 'Separation and Identification of Residual Diastereomers in a Maximally Labeled Triarylamine'. Together they form a unique fingerprint.

Cite this