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Small-Ring Compounds. XLVI. Stabilized Cyclopropylcarbinyl Anions. A Retro Cyclopropylcarbinyl-Allylcarbinyl Rearrangement

Maercker, Adalbert and Roberts, John D. (1966) Small-Ring Compounds. XLVI. Stabilized Cyclopropylcarbinyl Anions. A Retro Cyclopropylcarbinyl-Allylcarbinyl Rearrangement. Journal of the American Chemical Society, 88 (8). pp. 1742-1759. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151014-144942980

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Abstract

The cyclopropylcarbinyl anion is stabilized by a phenyl group attached to the carbinyl carbon toward ring opening, provided that potassium or sodium is the counterion. Replacement of potassium by lithium or magnesium in ether leads to immediate rearrangement and formation of the corresponding covalent allylcarbinyl organometallic compound. These rearrangements are reversible as can be demonstrated with diphenylcyclopropyl-carbinyllithium, which is stable in tetrahydrofuran but completely opened to y,y-diphenyllallylcarbinyllithium in diethyl ether. The retro rearrangement for this case can be achieved by simply adding tetrahydrofuran to the ether solution. The reaction of y,y-diphenylallylcarbinylmercuric bromide with potassium leads to ring closure with the formation of the corresponding cyclopropylcarbinylpotassium derivative.


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http://dx.doi.org/10.1021/ja00960a031DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00960a031PublisherArticle
Additional Information:© 1966 American Chemical Society. Received October 22, 1965. Supported in part by the National Science Foundation.
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Caltech Gates and Crellin Laboratories of Chemistry3279
Record Number:CaltechAUTHORS:20151014-144942980
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151014-144942980
Official Citation:Small-Ring Compounds. XLVI. Stabilized Cyclopropylcarbinyl Anions. A Retro Cyclopropylcarbinyl-Allylcarbinyl Rearrangement Adalbert Maercker and John D. Roberts Journal of the American Chemical Society 1966 88 (8), 1742-1759 DOI: 10.1021/ja00960a031
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61120
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:15 Oct 2015 20:10
Last Modified:15 Oct 2015 20:10

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