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Volumn 110, Issue 5, 1988, Pages 1356-1366

Cyclobutanediyls: A new class of localized biradicals. synthesis and epr spectroscopy

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBONS - SPECTROSCOPIC ANALYSIS; SPECTROSCOPY - APPLICATIONS;

EID: 0023977772     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00213a006     Document Type: Article
Times cited : (96)

References (52)
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    • Although they are generally not hydrocarbons, localized biradicals derived from Norrish type I and Norrish type II photoreactions are clearly relevant. An overview of early work involving primarily CIDNP (type I) and laser flash photolysis (type II) studies, as well as the dehydrobenzenes, is provided in Borden, W. T., Ed.; Wiley: New York A list of more recent works follows, which is not intended to be exhaustive. Type II biradicals: Scaiano, J. C. Acc. Chem. Res. 1982, 15, 252–258. Caldwell, R. A.; Majima, T.; Pac, C. J. Am. Chem. Soc. 1982, 104, 629–630. Scaiano, J. C.; Wagner, P. J. J. Am. Chem. Soc. 1984, 106, 4626–4627. Johnston, L. J.; Scaiano, J. C.; Sheppard, J. W.; Bays, J. P. Chem. Phys. Lett. 1986, 124, 493–498. Akiyama, K.; Ikegami, Y.; Tero-Kubota, S. J. Am. Chem. Soc. 1987, 109, 2538–2539. Type I biradicals and the hydrocarbon biradicals derived by CO loss: Caldwell, R. A.; Sakuragi, H.; Majima, T. J. Am. Chem. Soc. 1984, 106, 2471–2473. Weir, D.; Scaiano, J. C. Chem. Phys. Lett. 1985, 118, 526–529. Zimmt, M. B.; Doubleday, C., Jr.; Gould, I. R.; Turro, N. J. J. Am. Chem. Soc. 1985, 107, 6724–6726. Zimmt, M. B.; Doubleday, C., Jr.; Turro, N. J. J. Am. Chem. Soc. 1985, 107, 6726-6727; 1986, 108, 3618–3620. Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1986, 108, 2349–2353. Closs, G. L.; Forbes, M. D. E. J. Am. Chem. Soc. 1987, 109, 6185–6187. See also: Mizuno, K.; Ichinose, N.; Otsuji, Y.; Caldwell, R. A. J. Am. Chem. Soc. 1985, 107, 5797–5798. Sugawara, T.; Bethell, D.; Iwamura, H. Tetrahedron Lett. 1984, 25, 2375–2378. Localized, triplet biradicals can be trapped by dioxygen. See, for example: Wilson, R. M.; Geiser, F. J. Am. Chem. Soc. 1978, 100, 2225–2226.
    • Although they are generally not hydrocarbons, localized biradicals derived from Norrish type I and Norrish type II photoreactions are clearly relevant. An overview of early work involving primarily CIDNP (type I) and laser flash photolysis (type II) studies, as well as the dehydrobenzenes, is provided in: Dervan, P. B.; Dougherty, D. A. In Diradicals; Borden, W. T., Ed.; Wiley: New York, 1982; pp 107–149. A list of more recent works follows, which is not intended to be exhaustive. Type II biradicals: Scaiano, J. C. Acc. Chem. Res. 1982, 15, 252–258. Caldwell, R. A.; Majima, T.; Pac, C. J. Am. Chem. Soc. 1982, 104, 629–630. Scaiano, J. C.; Wagner, P. J. J. Am. Chem. Soc. 1984, 106, 4626–4627. Johnston, L. J.; Scaiano, J. C.; Sheppard, J. W.; Bays, J. P. Chem. Phys. Lett. 1986, 124, 493–498. Akiyama, K.; Ikegami, Y.; Tero-Kubota, S. J. Am. Chem. Soc. 1987, 109, 2538–2539. Type I biradicals and the hydrocarbon biradicals derived by CO loss: Caldwell, R. A.; Sakuragi, H.; Majima, T. J. Am. Chem. Soc. 1984, 106, 2471–2473. Weir, D.; Scaiano, J. C. Chem. Phys. Lett. 1985, 118, 526–529. Zimmt, M. B.; Doubleday, C., Jr.; Gould, I. R.; Turro, N. J. J. Am. Chem. Soc. 1985, 107, 6724–6726. Zimmt, M. B.; Doubleday, C., Jr.; Turro, N. J. J. Am. Chem. Soc. 1985, 107, 6726-6727; 1986, 108, 3618–3620. Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1986, 108, 2349–2353. Closs, G. L.; Forbes, M. D. E. J. Am. Chem. Soc. 1987, 109, 6185–6187. See also: Mizuno, K.; Ichinose, N.; Otsuji, Y.; Caldwell, R. A. J. Am. Chem. Soc. 1985, 107, 5797–5798. Sugawara, T.; Bethell, D.; Iwamura, H. Tetrahedron Lett. 1984, 25, 2375–2378. Localized, triplet biradicals can be trapped by dioxygen. See, for example: Wilson, R. M.; Geiser, F. J. Am. Chem. Soc. 1978, 100, 2225–2226.
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