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. doi:10.1021/ja00960a031. https://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.
| 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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| Issue or Number: | 8 | |||||||||
| DOI: | 10.1021/ja00960a031 | |||||||||
| Record Number: | CaltechAUTHORS:20151014-144942980 | |||||||||
| Persistent URL: | https://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: | 10 Nov 2021 22:44 |
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