Allenes as carbon nucleophiles in intramolecular ...

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Title Allenes as carbon nucleophiles in intramolecular attack on (pi-1,3-diene)palladium complexes: evidence for trans carbopalladation of the 1,3-diene
Author(s) I. Dorange, Jeanne Lofstedt, K. Narhi, J. Franzen, J. E. Backvall
Journal Chemistry (Weinheim an der Bergstrasse, Germany)
Date 2003
Volume 9
Issue 14
Start page 3445
End page 3449
Abstract Reaction of allene-substituted cyclohexa- and cyclohepta-1,3-dienes with [PdCl(2)(PhCN)(2)] gave eta(3)-(1,2,3)-cyclohexenyl- and eta(3)-(1,2,3)-cycloheptenylpalladium complexes, respectively, in which C-C bond formation between the allene and the 1,3-diene has occurred. Analysis of the (pi-allyl)palladium complexes by NMR spectroscopy, using reporter ligands, shows that the C-C bond formation has occurred by a trans carbopalladation involving nucleophilic attack by the middle carbon atom of the allene on a (pi-diene)palladium(II) complex. The stereochemistry of the (pi-allyl)palladium complexes was confirmed by benzoquinone-induced stereoselective transformations to allylic acetates.
DOI 10.1002/chem.200305056

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