Carbene Chemistry. I. Stereochemical Integrity at C sub Alpha in Ketone Tosylhydrazones. II. Hydrogen Migration in 2-Carbena-6,6-Dimethylnorbornane.
AIR FORCE INST OF TECH WRIGHT-PATTERSON AFB OHIO
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The tosylhydrazones of exo-3-deuteriocamphor and 2-deuterio-2-4-dimethyl-3-pentanone were treated with N-bromosuccinimide NBS and pyruvic acid to regenerate the parent ketones. The ketones from the pyruvic acid cleavage show a significant loss of deuterium. The ketones from the NBS cleavage show no loss of deuterium, indicating that stereochemical integrity at C sub alpha is maintained during the NBS cleavage.
- Organic Chemistry
- Physical Chemistry