Preparation and characterization of a bis-galvinoxyl-disulfide

Tetrahedron Letters

Volumn 37, Issue 49, 1996, Pages 8837-8840

  Shultz, David A ^a   Zhao, Qi ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; RADICAL;

ARTICLE; CYCLIC POTENTIOMETRY; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NONBIOLOGICAL MODEL; OXIDATION; PH; REACTION ANALYSIS;

EID: 0030566830     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02067-9     Document Type: Article

References (30)

1. 1. For references concerning molecule-based magnetism, see the following: (a) Iwamura, H. Pure & Appl. Chem. 1986, 58, 187;
2. (b) Iwamura, H. Pure Appl. Chem. 1987, 59, 1595;
3. (c) Iwamura, H. Adv. Phys. Org. Chem. 1990, 26, 179;
4. (d) Buchachenko, A.A. Russ. Chem. Rev. 1990, 59, 307;
5. (e) Gatteschi, D.; Kahn, O.; Miller, J.S.; Palacio, F. Adv. Mater. 1991, 3, 161;
6. (f) Iwamura, H.; Koga, N. Acc. Chem. Res. 1993, 26, 346;
7. (g) Day, P. Science 1993, 261, 431;
8. (h) Rajca, A. Chem. Rev. 1994, 94, 871;
9. (i) Gatteschi, D. Adv. Mater. 1994, 6, 635;
10. (j) Clément, R.; Lacroix, P.G.; O'Hare, D.; Evans, J. Adv. Mater. 1994, 6, 794;
11. (k) Miller, J.S.; Epstein, A.J. Angew. Chem. Int. Ed. Engl. 1994, 33, 385;
12. (l) Miller, J.S. Adv. Mater. 1994, 6, 322;
13. (m) Veciana, J.; Cirujeda, J.; Rovira, C.; Vidal-Gancedo, J. Adv. Mater. 1995, 7, 221;
14. (n) "Proceedings of the Symposium on Ferromagnetic and High Spin Based Materials," Miller, J.S.; Dougherty, D.A. Mol. Crys. Liq. Crys. 1989, 176
15. (o) "Proceedings of the Conference on Chemistry and Physics of Molecular Based Magnetic Materials," Iwamura, H.; Miller, J.S. Mol. Crys. Liq. Crys.1993, 180;
16. (p) "Proceedings of the Fourth International Conference on Molecule-Based Magnets," Miller, J.S.; Epstein, A.J. Mol. Crys. Liq. Crys.1995, 271-274;
17. (q) Gatteschi, D. Molecular Magnetic Materials; Kluwer Academic Publishers: Amsterdam, 1991;
18. (r) Kahn, O. Molecular Magnetism; VCH: New York, 1993;
19. (s) O'Connor, C.J. Research Frontiers in Magnetochemistry; World Scientific: Singapore, 1993.
20. 2. Biricik, V.W. Appl. Opt. 1989, 28, 1501.
21. 3. Visnovsky, S.; Kielar, P.; Nyvlt, M.; Parizek, V.; Flevaris, N.K.; Krishnan, R. IEEE Transactions on Magnetics 1993, 29, 3373.
22. 4. Shultz, D.A.; Tew, G., N, J. Org. Chem. 1994, 59, 6159.
23. 5. Kirste, B.; Grimm, M.; Kurreck, H. J. Am. Chem. Soc. 1989, 111, 108.
24. 6. Harrer, W.; Kurreck, H.; Reusch, J.; Gierke, W. Tetrahedron 1975, 31, 625.
25. 7. Volante, R.P. Tetrahedron Lett. 1981, 22, 3119.
26. 8. Atherton, N.M. Principles of Electron Spin Resonance; Ellis Horwood PTR Prentice Hall: New York, 1993.
27. 9. Wertz, J.E.; Bolton, J.R. Electron Spin Resonance; Chapman and Hall: New York, 1986.
28. 10. The EPR spectra of 6** are inconsistent with the formation of Yang's biradical by decomposition. Yang's biradical gives an S=1 spectrum at 77K (see: Mukai, D.; Ishizu, K. J. Chem. Phys. 1977, 66, 1680), while 6** gives a narrow doublet spectrum. The appearance of the EPR spectrum of 6** is also concentration independent, suggesting a lack of intermolecular interactions influencing the spectral shape.
29. 11. Experiments are underway to determine if this molecule exhibits temperature dependence of J-coupling. This "J-modulation" has been observed in transient biradicals, see: Forbes, M.D.E.; Schulz, G.R. J. Am. Chem. Soc. 1994, 116, 10174.
30. 12. Monolayers were prepared as described in ref. 4.