N,N′-dimethyl-N,N′-diarylurea anion radicals: An intramolecular reductive elimination

Journal of the American Chemical Society

Volumn 125, Issue 6, 2003, Pages 1460-1461

  Kurth, Todd L ^b   Lewis, Frederick D ^b   Hattan, Chris M ^a   Reiter, Richard C ^a   Stevenson, Cheryl D ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; DIMETHYLUREA; RADICAL; UREA DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; ELECTRON SPIN RESONANCE; MOLECULAR INTERACTION; REACTION ANALYSIS; REDUCTION;

EID: 0037433236     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0291890     Document Type: Article

References (28)

1. (a) Lepore, G.; Migdal, S.; Blagdon, D. E.; Goodman, M. J. Org. Chem. 1973, 38, 2590-2594.
2. (b) Tanatani, A.; Kagechika, H.; Azumaya, I.; Fukutomi, R.; Ito, Y.; Yamaguchi, K.; Shudo, K. Tetrahedron Lett. 1997, 38, 4425-4428.
3. Lewis, F. D.; Kurth, T. L.; Liu, W. Photochem. Photobiol. 2002, 1, 30-37.
4. (a) Bushey, M. L.; Hwang, A.: Stephens, P. W.; Nuckolls, C. J. Am. Chem. Soc. 2001, 123, 8157-8158.
5. (b) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683.
6. Salhi, F.; Lee, B.; Metz, C.; Bottomley, L. A.; Collard, D. M. Org. Lett. 2002, 4, 3195-3198.
7. Baumgarten, M.; Gherghel, L.; Friedrich, J.; Jurczok, M.; Rettig, W. J. Phys. Chem. A 2000, 104, 1130-1140.
8. Levin, G.: Jagur-Grodzinski, J.; Szwarc, M. J. Org. Chem. 1970, 35, 1702.
9. (a) Stevenson, C. D.; Echegoyen, L.; Lizardi, L. R. J. Phys. Chem. 1972, 76, 1439-1442.
10. (b) Shimada, K.; Szwarc, M. J. Am. Chem. Soc. 1975, 97, 3321-3323.
11. EPR spectra of the biphenyl and perdeuterated biphenyl anion radicals and mixtures of the two have been recorded. See: Stevenson, C. D.; Wehrmann, G. C., Jr.; Reiter, R. C. J. Phys. Chem. 1991, 95, 901-905.
12. Konishi, S.; Reddoch, A. H.; Leniart, D. S. J. Magn. Reson. 1977, 28, 41-51.
13. Hnoosh, M. H.; Zingaro, R. A. J. Am. Chem. Soc. 1970, 92, 4388-4395.
14. All EPR spectra were recorded with low modulation amplitude (0.05 G) and a low microwave power to avoid saturation.
15. Hs (each for 2Hs) corresponding to the spectrum for α,α′-binaphthyl radical anion in THF at 230 K are 4.36, 2.3, 1.69, 1.27, 0.91, 0.20. and 0.14 G.
16. Brumby, S. J. Magn. Reson. 1980, 40, 157-165.
17. (a) Dunkin, I. R.; Shields, C. J.; Quast, H. Tetrahedron 1989, 45, 259-268.
18. (b) Quast, H.; Bieber, L.; Danen, W. C. J. Am. Chem. Soc. 1978, 100, 1306-1307.
19. Biaryl radical anions have been produced via the reduction of tetraphenylmethane, triphenylamine, triphenylboron, triphenylphosphine oxide, phenyl ethers, diphenylsilanes, trinaphthylborane, etc. For references see: (a) Britt, A. D.; Urberg, M. M.; Kaiser, E. T. J. Org. Chem. 1966, 31, 1661-1662. (b) Wan, Y.-P.; O'Brien, D. H.; Smentowski, F. J. J. Am. Chem. Soc. 1972, 94, 7680-7686. (c) Shine, H. J.; Hughes, L. D.; Gesting, P. J. Organomet. Chem. 1970, 24, 53-62.
20. Biaryl radical anions have been produced via the reduction of tetraphenylmethane, triphenylamine, triphenylboron, triphenylphosphine oxide, phenyl ethers, diphenylsilanes, trinaphthylborane, etc. For references see: (a) Britt, A. D.; Urberg, M. M.; Kaiser, E. T. J. Org. Chem. 1966, 31, 1661-1662. (b) Wan, Y.-P.; O'Brien, D. H.; Smentowski, F. J. J. Am. Chem. Soc. 1972, 94, 7680-7686. (c) Shine, H. J.; Hughes, L. D.; Gesting, P. J. Organomet. Chem. 1970, 24, 53-62.
21. Biaryl radical anions have been produced via the reduction of tetraphenylmethane, triphenylamine, triphenylboron, triphenylphosphine oxide, phenyl ethers, diphenylsilanes, trinaphthylborane, etc. For references see: (a) Britt, A. D.; Urberg, M. M.; Kaiser, E. T. J. Org. Chem. 1966, 31, 1661-1662. (b) Wan, Y.-P.; O'Brien, D. H.; Smentowski, F. J. J. Am. Chem. Soc. 1972, 94, 7680-7686. (c) Shine, H. J.; Hughes, L. D.; Gesting, P. J. Organomet. Chem. 1970, 24, 53-62.
22. Gerson, F. Top. Curr. Chem. 1983, 115, 57-105.
23. Leffler, J. E.; Watts, G. B.; Tanigaki, T.; Dolan, E.; Miller, D. S. J. Am. Chem. Soc. 1970, 92, 6825-6830.
24. Cyclic voltammetry reveals only a single irreversible one-electron reduction.
25. (a) Miller, G. P.; Mack, J.; Briggs, J. Org. Lett. 2000, 2, 3983-3986.
26. (b) Prat, F.; Houk, K. N.: Foote, C. S. J. Am. Chem. Soc. 1998, 120, 845-846.
27. (c) Bjornholm, T.; Greve, D. R.; Reitzel, N.; Hassenkam, T.; Kjaer, K.; Howes, P. B.; Larsen, N. B.; Bogelund, J.; Jayaraman, M.; Ewbank, P. C.; McCullough, R. D. J. Am. Chem. Soc. 1998, 120, 7643-7644.
28. (d) Nakano, T.; Takewaki, K.; Yade, T.; Okamoto, Y. J. Am. Chem. Soc. 2001, 123, 9182-9183.