The autoxidation of optically active 1-bromo-2-methylbutane

doi:10.1139/V77-205

Paper

The autoxidation of optically active 1-bromo-2-methylbutane

Published May 1, 1977 · J. Howard, J. H. B. Chenier, D. A. Holden

Canadian Journal of Chemistry

3

Citations

0

Influential Citations

PDF

Abstract

(+)-1-Bromo-2-methylbutane undergoes autoxidation at 1 atm of oxygen and 30 °C to give, after reduction with triphenylphosphine, 1-bromo-2-methyl-2-butanol with a (+) to (−) enantiomer ratio of 1.9 ± 0.2. The optically active 1-bromo-2-methyl-2-butyl radical is, therefore, partially trapped by oxygen at this pressure before it has time to completely racemize. The half-life for racemization of the preferred conformation is approximately 2 × 10−8 s−1 at 30 °C. At 100 atm of oxygen the yield of (+)-CH3CH2COH(CH3)CH2Br is >90% and the reaction appears to proceed with retention of configuration. A small percentage of (−)-1-bromo-2-methyl-2-butanol is, however, still produced, presumably by inversion of configuration.

Study Snapshot

At 1 atm of oxygen and 30°C, (+)-1-bromo-2-methylbutane undergoes autoxidation to produce 1-bromo-2-methyl-2-butanol with a (+) to () enantiomer ratio of 1.9 0.2.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

The autoxidation of optically active 1-bromo-2-methylbutane

References

Citations