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, J. Lofstedt, K. Narhi, J. Franzen, J. 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 |
Using APA 6th Edition citation style.
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