BORON COMPOUND AS A TRAPPING REAGENT OF ALPHA-HYDROXY O-QUINODIMETHANES IN THE DIELS-ALDER REACTION

Authors
SHIMADA S OSODA K NARASAKA K
Citation
S. Shimada et al., BORON COMPOUND AS A TRAPPING REAGENT OF ALPHA-HYDROXY O-QUINODIMETHANES IN THE DIELS-ALDER REACTION, Bulletin of the Chemical Society of Japan, 66(4), 1993, pp. 1254-1257
Citations number
16
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
66
Issue
4
Year of publication
1993
Pages
1254 - 1257
Database
ISI
SICI code
0009-2673(1993)66:4<1254:BCAATR>2.0.ZU;2-F
Abstract
The Diels-Alder reaction of methyl 4-hydroxy-2-butenoate and alpha-hyd roxy o-quinodimethanes, generated from 1,2-dihydrobenzocyclobuten-1-ol derivatives by thermolysis, proceeds by the use of phenylboronic acid as a template. Boron reagents trap an alpha-hydroxy o-quinodimethane hylene-6-(1-hydroxyalkylidene)-1,3-cyclohexadiene) generated photochem ically from o-tolualdehyde and the Diels-Alder reaction with methyl 4- hydroxy-2-butenoate occurs to give the cycloadducts.