Electro-organic reactions. Part 52: Diels-Alder reactions in aqueous solution via electrogenerated quinodimethanes

Authors
Utley, JHP Oguntoye, E Smith, CZ Wyatt, PB
Citation
Jhp. Utley et al., Electro-organic reactions. Part 52: Diels-Alder reactions in aqueous solution via electrogenerated quinodimethanes, TETRAHEDR L, 41(37), 2000, pp. 7249-7254
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
37
Year of publication
2000
Pages
7249 - 7254
Database
ISI
SICI code
0040-4039(20000909)41:37<7249:ERP5DR>2.0.ZU;2-X
Abstract
ortho-Quinodimethanes (o-QDMs) are conveniently generated cathodically in a queous electrolyte in the presence of N-methylmaleimide, which acts as both redox mediator and dienophile. endo-Diels-Alder adducts are formed efficie ntly and rapidly and competition from electrohydrodimerisation of N-methylm aleimide is completely suppressed. Kinetic and coulometric evidence suggest s that initial electron transfer is to a complex between the o-QDM precurso r and N-methylmaleimide (hydrophobic packing). (C) 2000 Elsevier Science Lt d. All rights reserved.