Intramolecular C-H/C-D exchange in cofacially stacked polyfluorenes via electron-induced bond activation

Journal of the American Chemical Society

Volumn 127, Issue 15, 2005, Pages 5282-5283

  Stevenson, Cheryl D ^a   Kiesewetter, Matthew K ^a   Reiter, Richard C ^a   Abdelwahed, Sameh H ^b   Rathore, Rajendra ^b  

^a ILLINOIS STATE UNIVERSITY   (United States)

^b Marquette University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CARBON; FLUORENE DERIVATIVE; HYDROGEN; TRANSITION ELEMENT;

ARTICLE; CHEMICAL BOND; DISSOCIATION CONSTANT; ELECTRON SPIN RESONANCE; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR INTERACTION;

EID: 17644414917     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0432261     Document Type: Article

References (18)

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2. For examples, see: (a) Mitchell, G. P.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 7635-7636. (b) Mitchell, G. P.; Tilley, T. D. Angew. Chem., Int. Ed. 1998, 37, 2524-2526.
3. For examples, see: (a) Mitchell, G. P.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 7635-7636. (b) Mitchell, G. P.; Tilley, T. D. Angew. Chem., Int. Ed. 1998, 37, 2524-2526.
4. (a) To quote the experts: "In many cases, this rupture of a saturated bond is implied when the term 'activation' is used. Nevertheless, the splitting of the bond is actually a consequence of its activation, and it would be more correct to refer specifically to the splitting of the C-H bond in these situations." See: (a) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879-2932. Also see: (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245-269.
5. (a) To quote the experts: "In many cases, this rupture of a saturated bond is implied when the term 'activation' is used. Nevertheless, the splitting of the bond is actually a consequence of its activation, and it would be more correct to refer specifically to the splitting of the C-H bond in these situations." See: (a) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879-2932. Also see: (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245-269.
6. 1H NMR and X-ray crystallography, respectively. See: (a) Rathore, R.; Abdelwahed, S. H.; Guzei, L. A. J. Am. Chem. Soc. 2003, 125, 8712-8713. (b) Stevenson, C. D.; Echegoyen, L.; Lizardi, L. R. J. Phys. Chem. 1972, 76, 1439-1442. (c) Shimada, K.; Szwarc, M. J. Am. Chem. Soc. 1975, 97, 3321-3323.
7. 1H NMR and X-ray crystallography, respectively. See: (a) Rathore, R.; Abdelwahed, S. H.; Guzei, L. A. J. Am. Chem. Soc. 2003, 125, 8712-8713. (b) Stevenson, C. D.; Echegoyen, L.; Lizardi, L. R. J. Phys. Chem. 1972, 76, 1439-1442. (c) Shimada, K.; Szwarc, M. J. Am. Chem. Soc. 1975, 97, 3321-3323.
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18. After these very long time periods (weeks) there is a net loss of deuteriums to the solvent (H-D exchange between the anion radical and the HMPA). See: Stevenson, C. D.; Ballard, M. K.; Reiter, R. C. J. Org. Chem. 1991, 56, 4070.