Accession Number:

ADA063019

Title:

Carbene Chemistry. I. Stereochemical Integrity at C sub Alpha in Ketone Tosylhydrazones. II. Hydrogen Migration in 2-Carbena-6,6-Dimethylnorbornane.

Descriptive Note:

Master's thesis,

Corporate Author:

AIR FORCE INST OF TECH WRIGHT-PATTERSON AFB OHIO

Personal Author(s):

• Balyeat,John Robert

Report Date:

1978-02-22

Pagination or Media Count:

85.0

Abstract:

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.

Descriptors:

• *HYDROGEN
• *MIGRATION
• *STEREOCHEMISTRY
• *CARBENES
• THESES
• DEUTERIUM
• KETONES
• PENTANONES
• PYRUVIC ACID
• HYDRAZONES
• SUCCINIMIDES

Subject Categories:

• Organic Chemistry
• Physical Chemistry

Distribution Statement:

APPROVED FOR PUBLIC RELEASE