Olah, George A. ; Surya Prakash, G. K. ; Liang, Gao ; Westerman, Philip W. ; Kunde, Klaus ; Chandrasekhar, Jayaraman ; Schleyer, Paul V. R. (1980) Stable carbocations. 225. Proton and carbon-13 NMR spectroscopic study of 9-fluorenyl cations Journal of the American Chemical Society, 102 (13). pp. 4485-4492. ISSN 0002-7863
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Official URL: http://pubs.acs.org/doi/abs/10.1021/ja00533a030
Related URL: http://dx.doi.org/10.1021/ja00533a030
Abstract
A series of 9-substituted 9-fluorenyl cation were prepared and characterized by 1H and 13C NMR spectroscopy. Unsuccessful attempts were made to observe intramolecular interconversion of 9-methyl-9-fluorenyl cation via capped pyramidal ions with ring deuterated and methylated analogues. MINDO/3 calculations on isomeric structures of cyclopentadienyl, indenyl, and fluorenyl cations indicated strongly decreasing relative stabilities of the pyramidal forms due to benzoannulation. In deuterated fluorosulfonic acid solution, the 9-methyl-9-fluorenyl (1-CH3) and 3.9-dimethyl-9-fluorenyl cations (14) underwent hydrogen-deuterium exchange consistent with a protonation-deprotonation mechanism.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 7201 |
| Deposited On: | 25 Oct 2010 12:11 |
| Last Modified: | 08 Mar 2011 06:35 |
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