Palladium-catalyzed oxidations: Inhibition of a Pd-H elimination by coordination of a remote carbon-carbon double bond

Authors
Ait-Mohand, S Henin, F Muzart, J
Citation
S. Ait-mohand et al., Palladium-catalyzed oxidations: Inhibition of a Pd-H elimination by coordination of a remote carbon-carbon double bond, ORGANOMETAL, 20(8), 2001, pp. 1683-1686
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANOMETALLICS
ISSN journal
02767333 → ACNP
Volume
20
Issue
8
Year of publication
2001
Pages
1683 - 1686
Database
ISI
SICI code
0276-7333(20010416)20:8<1683:POIOAP>2.0.ZU;2-M
Abstract
Under oxidative conditions that use an anionic palladium salt as catalyst, cis-endo-2,3-bis(hydroxymethyl)bicyclo[2.2.1]hept-5-ene affords the corresp onding exo-lactol, while cis-endo-2,3-bis(hydroxymethyl)bicyclo[2.2.1]hepta ne provides the expected Lactone. Mechanistic considerations explain hero t he presence of the C=C bond blocks the oxidation at the lactol in the first case.