Published March 1, 1962
| public
Journal Article
Small-Ring Compounds. XXXVI. 3-Methylenecyclobutyl Bromide and 1-Methylcyclobut-2-enyl Bromide
- Creators
- Kiefer, Edgar F.
- Roberts, John D.
Abstract
3-Methylenecyclobutyl bromide and 1-methylcyclobut-2-enyl bromide have been synthesized from the cycloaddition products of allene with acrylonitrile and vinyl benzoate. The rate constants for solvolysis of the two bromides in aqueous ethanol have been determined and correlated with the solvolysis rates of a series of analogous bromides. 1-Methylcyclobut-2-enyl bromide appears to exhibit some rate enhancement due to cross-ring s-type interaction of the electrons formally centered on the 3-position with the electron-deficient 1-position in the transition state.
Additional Information
© 1962 American Chemical Society. Received June 10, 1961. Supported by the National Science Foundation and the Petroleum Research Fund of the American Chemical Society. Grateful acknowledgment is made to the Donors of the said Fund. National Science Foundation Predoctoral Fellow, 1958-1960.Additional details
- Eprint ID
- 61305
- DOI
- 10.1021/ja00864a021
- Resolver ID
- CaltechAUTHORS:20151020-083704601
- NSF
- American Chemical Society Petroleum Research Fund
- NSF Predoctoral Fellowship
- Created
-
2015-10-20Created from EPrint's datestamp field
- Updated
-
2021-11-10Created from EPrint's last_modified field
- Other Numbering System Name
- Caltech Gates and Crellin Laboratories of Chemistry
- Other Numbering System Identifier
- 2706