Sonochemical cycloadditions of o-quinones. The search for a cation radicalpathway

Authors
Avalos, M Babiano, R Bravo, JL Cabello, N Cintas, P Hursthouse, MB Jimenez, JL Light, ME Palacios, JC
Citation
M. Avalos et al., Sonochemical cycloadditions of o-quinones. The search for a cation radicalpathway, TETRAHEDR L, 41(21), 2000, pp. 4101-4105
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
21
Year of publication
2000
Pages
4101 - 4105
Database
ISI
SICI code
0040-4039(20000529)41:21<4101:SCOOTS>2.0.ZU;2-B
Abstract
Diels-Alder cycloadditions of an o-quinone monoketal with different furans, under argon, are considerably accelerated by ultrasonic irradiation. Moreo ver, these sonochemical reactions are regiospecific and proceed with a high diastereoselectivity. The results can be ascribed to the chemical role of ultrasounds which may favor a single electron transfer mechanism with respe ct to ionic or nonpolar pathways. (C) 2000 Elsevier Science Ltd. All rights reserved.