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Small-Ring Compounds. XLIV. Interconversion of Cyclopropylcarbinyl and Allylcarbinyl Grignard Reagents

Patel, Dinshaw J. and Hamilton, Carole L. and Roberts, John D. (1965) Small-Ring Compounds. XLIV. Interconversion of Cyclopropylcarbinyl and Allylcarbinyl Grignard Reagents. Journal of the American Chemical Society, 87 (22). pp. 5144-5148. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151015-104927941

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Abstract

The previously postulated rapid conversion of the cyclopropylcarbinyl Grignard reagent to the allylcarbinyl Grignard reagent has been confirmed by partial trapping of cyclopropylcarbinylmagnesium chloride prepared in refluxing diethyl ether in the presence of benzoic acid as methylcyclopropane and formation of cyclopropylcarbinylmagnesium bromide at - 24º from the corresponding bromide and magnesium in dimethyl ether. The rearrangement of cyclopropylcarbinylmagnesium bromide to allylcarbinylmagnesium bromide appears to be a first-order reaction and has a half-life of 121 min. at -24º.


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http://dx.doi.org/10.1021/ja00950a029DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00950a029PublisherArticle
Additional Information:© 1965 American Chemical Society. Received July 6, 1965. Supported in part by the National Science Foundation.
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Caltech Gates and Crellin Laboratories of Chemistry3522
Record Number:CaltechAUTHORS:20151015-104927941
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151015-104927941
Official Citation:Small-Ring Compounds. XLIV. Interconversion of Cyclopropylcarbinyl and Allylcarbinyl Grignard Reagents Dinshaw J. Patel, Carole L. Hamilton, and John D. Roberts Journal of the American Chemical Society 1965 87 (22), 5144-5148 DOI: 10.1021/ja00950a029
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61162
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:16 Oct 2015 19:03
Last Modified:16 Oct 2015 19:03

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