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Characterization and Reactivity of the [N,N-Dimethyl(thioformamidyl)]-9-fluorenyl Cation(1).
- Source :
-
The Journal of organic chemistry [J Org Chem] 1996 Oct 04; Vol. 61 (20), pp. 6805-6808. - Publication Year :
- 1996
-
Abstract
- The 9-[N,N-dimethyl(thioformamidyl)]-9-fluorenyl cation was generated under stable ion conditions and characterized by UV/visible and NMR spectroscopy and methanol trapping reactions. The same cation was generated by laser excitation of the appropriate chloride precursor in 2,2,2-trifluoroethanol, and rate constants for nucleophilic quenching by alcohols and several anions were measured. The quenching data for this and other 9-fluorenyl cations demonstrate that the reactivity decreases for 9-substituents in the order H > carbomethoxy > N,N-dimethyl(thioformamidyl), demonstrating that the thioamidyl group imparts substantial kinetic stabilization to an adjacent cationic center. Both steric and electronic factors are suggested to be important in determining this reactivity order.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 61
- Issue :
- 20
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 11667572
- Full Text :
- https://doi.org/10.1021/jo941685m