A new platinum complex catalyzed reaction involving nucleophilic substitution at the central carbon atom of the pi-allyl ligand

Citation
J. Kadota et al., A new platinum complex catalyzed reaction involving nucleophilic substitution at the central carbon atom of the pi-allyl ligand, J ORG CHEM, 64(20), 1999, pp. 7523-7527
Citations number
33
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
20
Year of publication
1999
Pages
7523 - 7527
Database
ISI
SICI code
0022-3263(19991001)64:20<7523:ANPCCR>2.0.ZU;2-X
Abstract
The reaction of 2-chloro-allyl acetate with sodium ethyl acetoacetate in th e presence of a platinum(O) complex gave furan derivatives. The key feature of this-new platinum-catalyzed reaction is the nucleophilic substitution a t the central carbon atom of pi-allyl complexes. The regioselectivity of th e nucleophilic attacks (central or terminal) is dependent on the pK(a) of t he nucleophile. In addition, a labeling experiment revealed that a rapid sy n-anti isomerization of the (pi-allyl) platinum complexes occurs.