Interplay of twisting and folding in overcrowded heteromerous bistricyclic aromatic enes

Amalia Levy, P. Ulrich Biedermann, Israel Agranat

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

(Formula presented) Flourenylidenexanthenes 5-7 were synthesized by 2-fold extrusion diazo-thione couplings. 7 exhibited yellow crystals and purple (560 nm) solutions. 1H NMR of 5 and 7 indicated subtle equilibria twisted (t) ⇌ anti-folded (a) major/minor conformations. 13C DNMR of 6 gave ΔGc‡(enantiomerization/inversion) = 26.5 kJ/mol and ΔGc‡(E,Z-topomerization) = 82.0 kJ/mol. PM3 calculations of 5 revealed minima a, t, ts (twisted/syn-folded), ΔΔHfo = 0.0, 14.1, 15.6 kJ/mol, and transition states [t-ts], [a-ts], [t], [a-a*], ΔΔHfo = 16.3, 17.4, 82.2, 99.3 kJ/mol.

Original languageEnglish
Pages (from-to)1811-1814
Number of pages4
JournalOrganic Letters
Volume2
Issue number13
DOIs
StatePublished - 29 Jun 2000
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Interplay of twisting and folding in overcrowded heteromerous bistricyclic aromatic enes'. Together they form a unique fingerprint.

Cite this