84519-69-7Relevant articles and documents
Asymmetric allylic oxidation of bridged-bicyclic alkenes using a copper-catalysed symmetrising-desymmetrising Kharasch-Sosnovsky reaction
Clark, J. Stephen,Clarke, Melanie-Rose,Clough, John,Blake, Alexander J.,Wilson, Claire
, p. 9447 - 9450 (2007/10/03)
Enantioselective symmetrising-desymmetrising allylic oxidation of racemic bridged bicyclic alkenes using an asymmetric copper-catalysed Kharasch-Sosnovsky reaction has been explored. Good yields and reasonable levels of induction (up to 70% ee) have been
2-Norbornanediazonium Ions Revisited
Kirmse, Wolfgang,Siegfried, Rainer
, p. 950 - 956 (2007/10/02)
The reactions of 2-norbornanediazonium ions have been reinvestigated with the aid of optically active and deuterium-labeled precursors.Enantiomeric purities were determined by direct VPC methods, and deuterium distributions by 2H NMR spectroscopy.The product pattern is strongly affected by the polarity of the solvent. exo-Diazonium ions 13 in water yield racemic exo alcohol (s,kΔ) of the norbornadiazonium ions.Optically active exo products are typical of nonpolar solvents and originate most probably from assymetric ion pairs.Model studies with optically active bicyclooct-3-en-2-amine (36) provide conclusive evidence that ion-pair colapse may lead to optically active products even in the case of delocalized achiral carbocations.