A cyclic oligophenylene containing two 1,8-naphthalene units bridged by two face to-face biphenyl linkages exhibiting unusual strain and pi-pi interaction

Authors
Iyoda, M Kondo, T Nakao, K Hara, K Kuwatani, Y Yoshida, M Matsuyama, H
Citation
M. Iyoda et al., A cyclic oligophenylene containing two 1,8-naphthalene units bridged by two face to-face biphenyl linkages exhibiting unusual strain and pi-pi interaction, ORG LETT, 2(14), 2000, pp. 2081-2083
Citations number
37
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
14
Year of publication
2000
Pages
2081 - 2083
Database
ISI
SICI code
1523-7060(20000713)2:14<2081:ACOCT1>2.0.ZU;2-H
Abstract
GRAPHICS 1,8-[1,8-Naphthalenediylbis(4',4-biphenyldiyl)]naphthalene, a very stable s trained cyclophane, has been synthesized in moderate yield using the copper -catalyzed coupling of 1,8-bis(4-(tributylstannyl)phenyl)naphthalene The X- ray analysis of the titled compound discloses bent p,p'-biphenylylene chain s with splayed naphthalene rings, and the p,p'-biphenylylene chains located face to face indicate a fairly strong pi-pi interaction.