Influence of palladium(II) complexes on the cycloaddition of alpha-bromoalkyl ketenes to cyclopentadiene

Authors
Fairlamb, IJS Dickinson, JM Cristea, IM
Citation
Ijs. Fairlamb et al., Influence of palladium(II) complexes on the cycloaddition of alpha-bromoalkyl ketenes to cyclopentadiene, TETRAHEDRON, 57(11), 2001, pp. 2237-2246
Citations number
57
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
11
Year of publication
2001
Pages
2237 - 2246
Database
ISI
SICI code
0040-4020(20010310)57:11<2237:IOPCOT>2.0.ZU;2-A
Abstract
Palladium(II) complexes, of the type PdL2X2 and PdX2, influence both the yi elds and endolexo ratio in formation of several 7-bromo-7-alkylbicyclo[3.2. 0]hept-2-en-6-ones. Standard dehydrochlorination of alpha -bromoacyl chlori des with triethylamine in the presence of cyclopentadiene and palladium cat alyst promotes the formation of the exo cycloadducts, which is accompanied by an improvement in the yields for both endo and exo cycloadducts. The mec hanism of the palladium-mediated cycloaddition is discussed. (C) 2001 Elsev ier Science Ltd. All rights reserved.