Published September 1950
| public
Journal Article
Rearrangements of Carbon Atoms in t-Butyl and t-Amyl Derivatives
Abstract
Rearrangements of the Wagner-Meerwein type of alkyl derivatives with polar catalysts are commonly considered to proceed through carbonium ion intermediates. Where such rearrangements may lead to several products, it is often possible to predict which product will be formed most readily by postulating that the most favorable sequence of carbonium ion intermediates should involve ions of maximum stability formed by successive 1,2-shifts of hydride or alkide ions. The order of carbonium ion stability (tertiary > secondary > primary) is usually inferred from the solvolytic reactivities of alkyl halides in ionizing (but weakly nucleophilic) solvents such as formic acid.
Additional Information
© 1950 American Chemical Society. Received February 7, 1950. We are indebted to Miss Winifred Bennett for the radioactivity determinations and to Mrs. Hildegarde Harris and Mrs. Rose Armstrong for help with some of with some of the experimental work. Supported in part by the joint program of the Office of Naval Research and the Atomic Energy Commission.Additional details
- Eprint ID
- 60673
- Resolver ID
- CaltechAUTHORS:20151001-104315082
- Office of Naval Research (ONR)
- Atomic Energy Commission
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2015-10-02Created from EPrint's datestamp field
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2021-11-10Created from EPrint's last_modified field