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Small-Ring Compounds. XLV. Influence of Vinyl and Phenyl Substituents on the Interconversion of Allylcarbinyl-Type Grignard Reagents

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. https://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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URLURL TypeDescription
http://dx.doi.org/10.1021/ja00960a030DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00960a030PublisherArticle
Additional Information:© 1966 American Chemical Society. Received October 22, 1965. Supported in part by the National Science Foundation.
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Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry3280
Issue or Number:8
Record Number:CaltechAUTHORS:20151014-144943480
Persistent URL:https://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:03 Oct 2019 09:04

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