Hill, E. Alexander and Richards, John H. (1961) Carbonium Ion Stabilization by Metallocene Nuclei. II. α-Metallocenylcarbonium Ions. Journal of the American Chemical Society, 83 (18). pp. 3840-3846. ISSN 0002-7863. doi:10.1021/ja01479a025. https://resolver.caltech.edu/CaltechAUTHORS:20150429-085400147
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Abstract
Acetates of methylferrocenylcarbinol, methylruthenocenylcarbinol and methylosmocenylcarbinol have been found to solvolyze with rates somewhat greater than trityl acetate, indicating a high stability for the corresponding carbomum ions. The solvolysis mechanism for methylferrocenylcarbinyl acetate has been carefully investigated to show that a carbonium ion mechanism is involved. Several possibilities for a molecular orbital description of direct metal participation are discussed. The order for carbonium ion stabilization (osmocenyl > ruthenocenyl > ferrocenyl) is found to parallel that of the strength of intramolecular hydrogen bonds to the carbinols, but is the reverse of that observed for reactivity of the parent metallocene toward acetylation.
| Item Type: | Article | |||||||||
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| Additional Information: | © 1961 American Chemical Society. Received February 28, 1961. | |||||||||
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| Issue or Number: | 18 | |||||||||
| DOI: | 10.1021/ja01479a025 | |||||||||
| Record Number: | CaltechAUTHORS:20150429-085400147 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20150429-085400147 | |||||||||
| Official Citation: | Carbonium Ion Stabilization by Metallocene Nuclei. II. α-Metallocenylcarbonium Ions E. Alexander Hill and John H. Richards Journal of the American Chemical Society 1961 83 (18), 3840-3846 DOI: 10.1021/ja01479a025 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 57080 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Tony Diaz | |||||||||
| Deposited On: | 01 May 2015 17:18 | |||||||||
| Last Modified: | 10 Nov 2021 21:07 |
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