Study on the scope of tert-amino effect: New extensions of type 2 reactions to bridged biaryls

Paola Bottino, Petra Dunkel, Michele Schlich, Lorenzo Galavotti, Ruth Deme, Géza Regdon, Attila Bényei, Klára Pintye-Hódi, Giuseppe Ronsisvalle, Péter Mátyus

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Thermal isomerization of aminomethyl- or oxygen-bridged biphenyl systems possessing dicyanovinyl and sec-amino groups in ortho- and ortho0-positions was investigated. Both systems underwent cyclization via tert-amino effect. Thus, 2-(2-{[2-(sec-amino)benzyl]-N-methylamino}benzylidene)malononitriles gave tetrahydroquinolines, whereas a 2-[2-(sec-amino)phenoxy]benzylidenemalononitrile isomerized to dibenzoxazonine derivative. The ring closure reaction was studied by differential scanning calorimetry measurements.

Original languageEnglish
Pages (from-to)1033-1041
Number of pages9
JournalJournal of Physical Organic Chemistry
Volume25
Issue number11
DOIs
Publication statusPublished - Nov 1 2012

    Fingerprint

Keywords

  • Dibenzoxazonine
  • Differential scanning calorimetry
  • Hydrogen migration
  • Isomerization
  • Oxazonine
  • Tert-amino effect
  • Tetrahydroquinoline

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this