REACTIONS OF A NOVEL BENZYNE ANNELATED WITH 2 BICYCLO[2.2.2]OCTENE UNITS

Authors
MATSUURA A NISHINAGA T KOMATSU K
Citation
A. Matsuura et al., REACTIONS OF A NOVEL BENZYNE ANNELATED WITH 2 BICYCLO[2.2.2]OCTENE UNITS, Tetrahedron letters, 38(23), 1997, pp. 4125-4128
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
23
Year of publication
1997
Pages
4125 - 4128
Database
ISI
SICI code
0040-4039(1997)38:23<4125:ROANBA>2.0.ZU;2-X
Abstract
Anthranilic acid 9 and o-dibromobenzene 14 annelated with two bicyclo[ 2.2.2]octene units were synthesized as the precursors for titled benzy ne 3. The generation of 3 was confirmed by trapping with furan and its derivative. In the absence of trapping agent, benzyne 3 generated by diazotization of 9 gave acridone 12 while that generated via lithiatio n of 14 dimerized to give BCO-annelated biphenylene 11. The HOMO level of 11 is considerably raised as shown by cyclic voltammetry. (C) 1997 Elsevier Science Ltd.