Structure-property relationships in trimethylenemethane-type biradicals. 2. Synthesis and EPR spectral characterization of dinitroxide biradicals

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4386-4396

  Shultz, David A ^a   Boal, Andrew K ^a   Lee, Hyoyoung ^a   Farmer, Gary T ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METHANE; NITROXIDE; RADICAL;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ELECTRON SPIN RESONANCE; MOLECULAR DYNAMICS; MOLECULAR MODEL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033546107     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990061j     Document Type: Article

References (83)

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2. For papers discussing the effects of torsion on exchange coupling in m-phenylene-type biradicals, see: (a) Dvolaitzky, M.; Chiarelli, R.; Rassat, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 180. (b) Kanno, F.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1993, 115, 847. Silverman, S. K.; Dougherty, D. A. J. Phys. Chem. 1993, 97, 13273. Okada, K.; Matsumoto, K.; Oda, M.; Murai, H.; Akiyama, K.; Ikegami, Y. Tetrahedron Lett. 1995, 36, 6693. (e) Adam, W.; van Barneveld, C.; Bottle, S. E.; Engert, H.; Hanson, G. R.; Harrer, H. M.; Heim, C.; Nau, W. M.; Wang, D. J. Am. Chem. Soc. 1996, 118, 3974. (f) Fujita, J.; Tanaka, M.; Suemune, H.; Koga, N.; Matsuda, K.; Iwamura, H. J. Am. Chem. Soc. 1996, 118, 9347. (g) Okada, K.; Imakura, T.; Oda, M.; Murai, H.; Baumgarten, M. J. Am. Chem. Soc. 1996, 118, 3047. (h) See also ref 11. Ab initio calculations explain antiferromagnetic coupling in certain m-phenylene-linked structures, see: Fang, S.; Lee, M.-S.; Hrovat, D. A.; Borden, W. T. J. Am. Chem Soc. 1995, 117, 6727.
3. For papers discussing the effects of torsion on exchange coupling in m-phenylene-type biradicals, see: (a) Dvolaitzky, M.; Chiarelli, R.; Rassat, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 180. (b) Kanno, F.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1993, 115, 847. Silverman, S. K.; Dougherty, D. A. J. Phys. Chem. 1993, 97, 13273. Okada, K.; Matsumoto, K.; Oda, M.; Murai, H.; Akiyama, K.; Ikegami, Y. Tetrahedron Lett. 1995, 36, 6693. (e) Adam, W.; van Barneveld, C.; Bottle, S. E.; Engert, H.; Hanson, G. R.; Harrer, H. M.; Heim, C.; Nau, W. M.; Wang, D. J. Am. Chem. Soc. 1996, 118, 3974. (f) Fujita, J.; Tanaka, M.; Suemune, H.; Koga, N.; Matsuda, K.; Iwamura, H. J. Am. Chem. Soc. 1996, 118, 9347. (g) Okada, K.; Imakura, T.; Oda, M.; Murai, H.; Baumgarten, M. J. Am. Chem. Soc. 1996, 118, 3047. (h) See also ref 11. Ab initio calculations explain antiferromagnetic coupling in certain m-phenylene-linked structures, see: Fang, S.; Lee, M.-S.; Hrovat, D. A.; Borden, W. T. J. Am. Chem Soc. 1995, 117, 6727.
4. For papers discussing the effects of torsion on exchange coupling in m-phenylene-type biradicals, see: (a) Dvolaitzky, M.; Chiarelli, R.; Rassat, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 180. (b) Kanno, F.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1993, 115, 847. Silverman, S. K.; Dougherty, D. A. J. Phys. Chem. 1993, 97, 13273. Okada, K.; Matsumoto, K.; Oda, M.; Murai, H.; Akiyama, K.; Ikegami, Y. Tetrahedron Lett. 1995, 36, 6693. (e) Adam, W.; van Barneveld, C.; Bottle, S. E.; Engert, H.; Hanson, G. R.; Harrer, H. M.; Heim, C.; Nau, W. M.; Wang, D. J. Am. Chem. Soc. 1996, 118, 3974. (f) Fujita, J.; Tanaka, M.; Suemune, H.; Koga, N.; Matsuda, K.; Iwamura, H. J. Am. Chem. Soc. 1996, 118, 9347. (g) Okada, K.; Imakura, T.; Oda, M.; Murai, H.; Baumgarten, M. J. Am. Chem. Soc. 1996, 118, 3047. (h) See also ref 11. Ab initio calculations explain antiferromagnetic coupling in certain m-phenylene-linked structures, see: Fang, S.; Lee, M.-S.; Hrovat, D. A.; Borden, W. T. J. Am. Chem Soc. 1995, 117, 6727.
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