INFIQC 05475
INSTITUTO DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Unidad Ejecutora - UE
artículos
Título:
Reactions of Halonorbornane and oxo-substitued derivatives with Different Anions
Autor/es:
JORGE G. URANGA, ANA N. SANTIAGO
Revista:
NEW JOURNAL OF CHEMISTRY
Editorial:
ROYAL SOC CHEMISTRY
Referencias:
Lugar: Gainesville, USA; Año: 2010
ISSN:
1144-0546
Resumen:
Reactions of 2-bromo-, 2-chloronorbornane, 3-chloronorbornan-2-one and 3-bromocamphor with Me3Sn-, Ph2P- or PhS- ions were studied by the SRN1 mechanism in liquid ammonia or DMSO. Results show that substrates having a carbonyl group facilitate electron transfer reactions, which are impeded in absence of such group. However, when the free radical formed is stabilized by conjugation, the coupling reaction decreases, causing a concomitant increase in the reduction product. Theoretical studies explained the observed reactivity on the basis of a mechanism involving reductive cleavage as a function of the ð-ó interactions
