Howden, Merlin E. H. and Maercker, Adalbert and Burdon, James and Roberts, John D. (1966) Small-Ring Compounds. XLV. Influence of Vinyl and Phenyl Substituents on the Interconversion of Allylcarbinyl-Type Grignard Reagents. Journal of the American Chemical Society, 88 (8). pp. 1732-1742. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151014-144943480
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Abstract
Equilibration of the α and β positions in y,y-diphenylallylcarbinylmagnesium bromide was complete after 5 hr at room temperature. Less than 0.3% of the isomeric cyclopropylcarbinyl derivative, however, is in equilibrium with the ring-opened species. While reactions of the Grignard reagents normally expected to have anionic-type mechanisms were found to lead to allylcarbinyl products only, substantial amounts of cyclic products were formed with molecular oxygen.
| Item Type: | Article | |||||||||
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| Additional Information: | © 1966 American Chemical Society. Received October 22, 1965. Supported in part by the National Science Foundation. | |||||||||
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| Record Number: | CaltechAUTHORS:20151014-144943480 | |||||||||
| Persistent URL: | http://resolver.caltech.edu/CaltechAUTHORS:20151014-144943480 | |||||||||
| Official Citation: | Small-Ring Compounds. XLV. Influence of Vinyl and Phenyl Substituents on the Interconversion of Allylcarbinyl-Type Grignard Reagents Merlin E. H. Howden, Adalbert Maercker, James Burdon, and John D. Roberts Journal of the American Chemical Society 1966 88 (8), 1732-1742 DOI: 10.1021/ja00960a030 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 61122 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 15 Oct 2015 17:24 | |||||||||
| Last Modified: | 15 Oct 2015 17:24 |
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