Synthesis and characterization of a planarized, trimethylenemethane-type bis(semiquinone) biradical

Tetrahedron

Volumn 55, Issue 41, 1999, Pages 12079-12086

  Shultz, David A ^a   Lee, Hyoyoung ^a   Fico Jr , Rosario M ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

Benzoquinone; Conformation; Electrochemistry; Molecular design; Radicals

Indexed keywords

CYCLOPROPANE; METHANE; SEMIQUINONE;

ARTICLE; CHEMICAL BOND; CONFORMATIONAL TRANSITION; POTENTIOMETRY; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033536675     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00714-0     Document Type: Article

References (30)

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3. (c) Dougherty, D.A. Acc. Chem. Res. 1991, 24, 88;
4. (d) Iwamura, H. Pure & Appl. Chem. 1993, 65, 57;
5. (e) Jacobs, S.J.; Shultz, D.A.; Jain, R.; Novak, J.; Dougherty, D.A. J. Am. Chem. Soc. 1993, 115, 1744;
6. (f) Rajca, A. Chem. Rev. 1994, 94, 871;
7. (g) Borden, W.T.; Iwamura, H.; Berson, J.A. Acc. Chem. Res. 1994, 24, 109;
8. (h) West, A.P., Jr.; Silverman, S.K.; Dougherty, D.A. J. Am. Chem. Soc. 1996. 118, 1452;
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10. (j) Borden, W.T.; Davidson, E.R. Acc. Chem. Res. 1996, 29, 67;
11. (k) Shultz, D.A. In Magnetic Properties of Organic Materials; P. Lahti, Ed.; Marcel Dekker, Inc.: New York, 1999.
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13. (b) Shultz, D.A.; Boal, A.K.; Driscoll, D.J.; Kitchin, J.R.; Tew, G.N. J. Org. Chem. 1995, 60, 3578;
14. (c) Shultz, D.A.; Boal, A.K.; Driscoll, D.J.; Farmer, G.T.; Hollomon, M.G.; Kitchin, J.R.; Miller, D.B.; Tew, G.N. Mol. Cryst. Liq. Cryst. 1997, 505, 303.
15. Shultz, D.A.; Bodnar, S.H. Inorg. Chem. 1999, 38, 591.
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17. Shultz, D.A. In Magnetic Properties of Organic Materials; P. Lahti, Ed.; Marcel Dekker, Inc.: New York, 1999.
18. Shultz, D.A.; Boal, A.K.; Lee, H.; Farmer, G.T. J. Org. Chem. 1999, 64, in press.
19. Marquez, J.; Moreno-Mañas, M. Chem. Lett. 1981, 173.
20. Direct formation of ene-dione by condensation of the ketone derived from oxication of and acetylacetone according to the method of Lehnen failed (Lehnen, W. Tetrahedron 1973, 29, 635). However, this method was for Knovenagel reaction of diethylmalonate and benzophenone derivatives.
21. 3 (Imamoto, T.; Takiyama, N.; Nakamura, K. Tetrahedron Lett. 1985, 26, 4763) gave only very small amounts of the desired diol.
22. 3 (Imamoto, T.; Takiyama, N.; Nakamura, K. Tetrahedron Lett. 1985, 26, 4763) gave only very small amounts of the desired diol.
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29. For an excellent discussion of the salient features of the Curie plot, see: The Chemistry of Quinonoid Compounds, Vol. II; Berson, J.A., Ed.; John Wiley & Sons: New York, 1988, pp. 473-489.
30. Shultz, D.A.; Farmer, G.T. J. Org. Chem. 1998, 63, 6254.