Nonplanar Aromatic Compounds. 9. Synthesis, Structure, and Aromaticity of 1:2,13:14-Dibenzo[2]paracyclo[2](2,7)- pyrenophane-1,13-diene

Baozhong Zhang,† Gregory P. Manning,† Michał A. Dobrowolski,‡ Michał K. Cyrański,‡ and Graham J. Bodwell*†
Department of Chemistry, Memorial University, St. John's, Newfoundland, Canada A1B 3X7, and Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
Org. Lett., 2008, 10 (2), pp 273–276
DOI: 10.1021/ol702703b
Publication Date (Web): December 19, 2007
Copyright © 2008 American Chemical Society
†

 Memorial University.

,
‡

 University of Warsaw.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, gbodwell@mun.ca

Abstract

Abstract Image

Pyrenophane (6) and an octaphenyl derivative (16) were synthesized using two different routes. Both cyclophanes contain a severely bent pyrene unit (6:  θ = 93.6° and 16:  θ = 95.8°, according to DFT-calculations (B3LYP/6-311G**)), which was generated at room temperature by a valence isomerization/dehydrogenation (VID) reaction. HOMA and NICS indicate 92−98% retention of aromaticity of the highly distorted pyrene systems compared to planar pyrene.

View: Full Text HTML | Hi-Res PDF | PDF w/ Links

Tools

History

  • Published In Issue January 17, 2008
  • Received November 7, 2007

Recommend & Share

Related Content

Other ACS content by these authors: