Thermal cycloaddition reactions of azulene-1,5-quinones and azulene-1,7-quinones with cyclic dienes and cycloheptatriene

Citation
A. Mori et al., Thermal cycloaddition reactions of azulene-1,5-quinones and azulene-1,7-quinones with cyclic dienes and cycloheptatriene, J CHEM S P1, (15), 1999, pp. 2129-2141
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
15
Year of publication
1999
Pages
2129 - 2141
Database
ISI
SICI code
0300-922X(19990807):15<2129:TCROAA>2.0.ZU;2-5
Abstract
[2+4]-[6+4] Cycloadducts were obtained from the thermal cycloaddition react ions of azulenequinones with cyclic 4 pi systems such as 1,3-diphenylisoben zofuran and isobenzofuran while the reaction of cycloheptatriene and azulen equinones gave ene products as well as cage molecules. The first addition s ite of 1,3-diphenylisobenzofuran was different for 3-bromoazulene-1,5-quino ne and azulene-1,5-quinone; the former reacted on the cyclopentenone part a nd the latter on the C-6-C-7 bond to avoid formation of an unstable cyclope ntadienone structure.