A New Platinum Complex Catalyzed Reaction Involving Nucleophilic Substitution at the Central Carbon Atom of the π-Allyl Ligand

The reaction of 2-chloro-allyl acetate with sodium ethyl acetoacetate in the presence of a platinum(0) complex gave furan derivatives. The key feature of this new platinum-catalyzed reaction is the nucleophilic substitution at the central carbon atom of π-allyl complexes. The regioselectivity of the...

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Bibliographic Details
Published in:Journal of organic chemistry 1999-10, Vol.64 (20), p.7523-7527
Main Authors: Kadota, Joji, Komori, Shinji, Fukumoto, Yoshiya, Murai, Shinji
Format: Article
Language:English
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Summary:The reaction of 2-chloro-allyl acetate with sodium ethyl acetoacetate in the presence of a platinum(0) complex gave furan derivatives. The key feature of this new platinum-catalyzed reaction is the nucleophilic substitution at the central carbon atom of π-allyl complexes. The regioselectivity of the nucleophilic attacks (central or terminal) is dependent on the pK a of the nucleophile. In addition, a labeling experiment revealed that a rapid syn−anti isomerization of the (π-allyl) platinum complexes occurs.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo990845x