Small-Ring Compounds. XLVI. Stabilized Cyclopropylcarbinyl Anions. A Retro Cyclopropylcarbinyl-Allylcarbinyl Rearrangement
- Creators
- Maercker, Adalbert
- Roberts, John D.
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.
Additional Information
© 1966 American Chemical Society. Received October 22, 1965. Supported in part by the National Science Foundation.Additional details
- Eprint ID
- 61120
- DOI
- 10.1021/ja00960a031
- Resolver ID
- CaltechAUTHORS:20151014-144942980
- NSF
- Created
-
2015-10-15Created from EPrint's datestamp field
- Updated
-
2021-11-10Created from EPrint's last_modified field
- Other Numbering System Name
- Caltech Gates and Crellin Laboratories of Chemistry
- Other Numbering System Identifier
- 3279