Anion Radicals of Di-trans-[12]annulene and Heptalene in a One-Pot Synthesis from a Common Fire Retardant

Organic Letters

Volumn 6, Issue 3, 2004, Pages 393-396

  Gard, Matthew N ^a   Reiter, Richard C ^a   Stevenson, Cheryl D ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,5,6,9,10 HEXABROMOCYCLODODECANE; ALKENE DERIVATIVE; ANNULENE DERIVATIVE; CARBON; FLAME RETARDANT; IODINE; POTASSIUM DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CONFORMATION; DENSITY; ELECTRON; ELECTRON SPIN RESONANCE; HALOGENATION; LOW TEMPERATURE; MOLECULAR DYNAMICS; REOXYGENATION; SCALE UP; SYNTHESIS;

EID: 1342264150     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0362921     Document Type: Article

References (21)

1. Wiberg, K. B. Chem. Rev. 2001, 101, 1317.
2. (a) Peters, S. J.; Turk, M. R.; Kiesewetter, M. K.; Reiter, R. C.; Stevenson, C. D. J. Am. Chem. Soc. 2003, 125, 11212.
3. (b) Broadus, K. M.; Kass, S. R. J. Am. Chem. Soc. 2000, 122, 10697.
4. (c) Broadus, K. M.; Kass, S. R. J. Am. Chem. Soc. 2001, 123, 4189.
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7. 2a
8. Weil, J. A.; Bolton, J. R.; Wertz, J. E. Electron Paramagnetic Resonance: Elementary Theory and Practical Applications; Wiley: New York, 1994.
9. Peters, S. J.; Turk, M. R.; Kiesewetter, M. K.; Stevenson, C. D. J. Am. Chem. Soc. 2003, 125, 11264.
10. Biaryl radical anions have been produced via the reduction of tetraphenylmethane, triphenylamine, triphenylboron, triphenylphosphine oxide, phenyl ethers, diphenylsilanes, trinaphthyl borane, biarylureas, etc. For references, see: (a) Britt, A. D.; Urberg, M. M.; Kaiser, E. T. J. Org. Chem. 1966, 31, 1661. (b) Wan, Y.-P.; O'Brien, D. H.; Smentowski, F. J. J. Am. Chem. Soc. 1972, 94, 7680. (c) Shine, H. J.; Hughes, L. D.; Gesting, P. J. Organomet. Chem. 1970, 24, 53. (d) Lewis, F. D.; Kurth, T. L.; Hattan, C. M.; Reiter, R. C.; Stevenson, C. D. J. Am. Chem. Soc. 2003, 125, 1460. (e) Gerson, F. Top. Curr. Chem. 1983, 115, 57.
11. Biaryl radical anions have been produced via the reduction of tetraphenylmethane, triphenylamine, triphenylboron, triphenylphosphine oxide, phenyl ethers, diphenylsilanes, trinaphthyl borane, biarylureas, etc. For references, see: (a) Britt, A. D.; Urberg, M. M.; Kaiser, E. T. J. Org. Chem. 1966, 31, 1661. (b) Wan, Y.-P.; O'Brien, D. H.; Smentowski, F. J. J. Am. Chem. Soc. 1972, 94, 7680. (c) Shine, H. J.; Hughes, L. D.; Gesting, P. J. Organomet. Chem. 1970, 24, 53. (d) Lewis, F. D.; Kurth, T. L.; Hattan, C. M.; Reiter, R. C.; Stevenson, C. D. J. Am. Chem. Soc. 2003, 125, 1460. (e) Gerson, F. Top. Curr. Chem. 1983, 115, 57.
12. Biaryl radical anions have been produced via the reduction of tetraphenylmethane, triphenylamine, triphenylboron, triphenylphosphine oxide, phenyl ethers, diphenylsilanes, trinaphthyl borane, biarylureas, etc. For references, see: (a) Britt, A. D.; Urberg, M. M.; Kaiser, E. T. J. Org. Chem. 1966, 31, 1661. (b) Wan, Y.-P.; O'Brien, D. H.; Smentowski, F. J. J. Am. Chem. Soc. 1972, 94, 7680. (c) Shine, H. J.; Hughes, L. D.; Gesting, P. J. Organomet. Chem. 1970, 24, 53. (d) Lewis, F. D.; Kurth, T. L.; Hattan, C. M.; Reiter, R. C.; Stevenson, C. D. J. Am. Chem. Soc. 2003, 125, 1460. (e) Gerson, F. Top. Curr. Chem. 1983, 115, 57.
13. Biaryl radical anions have been produced via the reduction of tetraphenylmethane, triphenylamine, triphenylboron, triphenylphosphine oxide, phenyl ethers, diphenylsilanes, trinaphthyl borane, biarylureas, etc. For references, see: (a) Britt, A. D.; Urberg, M. M.; Kaiser, E. T. J. Org. Chem. 1966, 31, 1661. (b) Wan, Y.-P.; O'Brien, D. H.; Smentowski, F. J. J. Am. Chem. Soc. 1972, 94, 7680. (c) Shine, H. J.; Hughes, L. D.; Gesting, P. J. Organomet. Chem. 1970, 24, 53. (d) Lewis, F. D.; Kurth, T. L.; Hattan, C. M.; Reiter, R. C.; Stevenson, C. D. J. Am. Chem. Soc. 2003, 125, 1460. (e) Gerson, F. Top. Curr. Chem. 1983, 115, 57.
14. Biaryl radical anions have been produced via the reduction of tetraphenylmethane, triphenylamine, triphenylboron, triphenylphosphine oxide, phenyl ethers, diphenylsilanes, trinaphthyl borane, biarylureas, etc. For references, see: (a) Britt, A. D.; Urberg, M. M.; Kaiser, E. T. J. Org. Chem. 1966, 31, 1661. (b) Wan, Y.-P.; O'Brien, D. H.; Smentowski, F. J. J. Am. Chem. Soc. 1972, 94, 7680. (c) Shine, H. J.; Hughes, L. D.; Gesting, P. J. Organomet. Chem. 1970, 24, 53. (d) Lewis, F. D.; Kurth, T. L.; Hattan, C. M.; Reiter, R. C.; Stevenson, C. D. J. Am. Chem. Soc. 2003, 125, 1460. (e) Gerson, F. Top. Curr. Chem. 1983, 115, 57.
15. Mullen, K. Helv. Chim. Acta 1974, 57, 2399.
16. Stevenson, C. D.; Kim, Y. S. J. Am. Chem. Soc. 2000, 122, 3211.
17. (a) Hrovat, D. A.; Hammons, J. A.; Stevenson, C. D.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 9523.
18. (b) Kurth, T. L.; Brown, E. C.; Hattan, C. M.; Reiter, R. C.; Stevenson, C. D. J. Phys. Chem. A 2002, 106, 478.
19. Rounding off to two significant figures (corresponding to the experimental error) makes some of the calculated spin densities appear degenerate.
20. The interchange of spins in this time frame causes line width modulation in EPR spectra; see ref 10 and Franekel, G. K. J. Phys. Chem. 1967, 71, 139.
21. Stevenson, C. D.; Gard, M. N.; Reiter, R. C. J. Org. Chem. 2003, 68, 1464.