Reduction of C Bonds Proceeds with Retention of Configuration: Stereochemical Investigation of the Heterogeneous Reduction by Dideuterium of (Homohypostrophene)Neopentyl(2-Norbornyl)Platinum(II) Complexes on Platinum Black.
Abstract
This paper reports an investigation of the heterogeneous, platinum ( 0)-catalyzed reductions by dideuterium of (homohypostrophene)neopentyl(exo-2- norbornyl)platinum(II) and (Homohypostrophene)neopentyl(endo-2-norbornyl) platinum(II). The stereochemistries of bonding of the norbornyl groups to platinum are rigorously defined by crystal structures. The reductions occur on the surface of the catalyst: the organic ligands are converted to alkanes via reaction of surface alkyls with surface deuterides (D); the platinum atom in the organometallic complex is reduced to platinum(0), and becomes part of the surface of the catalyst. Reduction incorporates deuterium into the exo-2 position of norbornane; analogous reduction of 2 incorporates deuterium predominantly into the endo-2 position of norbornane. These results provide the most direct evidence now available that the stereochemistry of the reduction of C bonds by H (D) proceeds with retention of configuration.
Document Details
- Document Type
- Technical Report
- Publication Date
- Apr 23, 1991
- Accession Number
- ADA235515
Entities
People
- Derk A. Wierda
- George M. Whitesides
- Taylor R. Lee
Organizations
- Massachusetts Institute of Technology