3,5-Di-tert-butyl-3'-(N-tert-butyl-N-aminoxy)-4-oxybiphenyl: A heterospin diradical with temperature dependent behavior

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5176-5182

  Liao, Yi ^a   Xie, Chunping ^a   Lahti, Paul M ^a   Weber, Ralph T ^b   Jiang, JinJie ^b   Barr, David P ^b  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b Bruker Instruments Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RADICAL;

ARTICLE; CHEMICAL INTERACTION; CONFORMATIONAL TRANSITION; ELECTRON SPIN RESONANCE; HEAT TREATMENT; SYNTHESIS; THERMOSTABILITY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0032997442     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990317l     Document Type: Article

References (34)

1. Diradicals; Borden, W. T., Ed.; John Wiley and Sons: New York, 1982.
2. Michl, J.; Bonacic-Koutecky, V. Tetrahedron 1988, 24, 7559.
3. Longuet-Higgins, H. C. J. Chem. Phys. 1950, 18, 265, 275, 283.
4. Longuet-Higgins, H. C. In Theoretical Organic Chemistry, Kekule Symposium; Butterworth: London, 1958; pp 9-19.
5. Klein, D. J.; Nelin, C. J.; Alexander, S.; Matsen, F. E. J. Chem. Phys. 1982, 77, 3101.
6. Klein, D. J. Pure Appl. Chem. 1983, 55, 299.
7. Misurkin, I. A.; Ovchinnikov, A. A. Russ. Chem. Res. (Engl.) 1977, 46, 967.
8. Ovchinnikov, A. A. Theor. Chim. Acta 1978, 47, 297.
9. Borden, W. T.; Davidson, E. R. J. Am. Chem. Soc. 1977, 99, 4587.
10. Rule, M.; Matlin, A. R.; Seeger, D. E.; Hilinski, E. F.; Dougherty, D. A.; Berson, J. A. Tetrahedron 1982, 38, 787.
11. Horvat, D. A.; Murcko, M. A.; Lahti, P. M.; Borden, W. T. J. Chem. Soc., Perkin Trans. 2 1998, 1037.
12. Dvolaitzky, M.; Chiarelli, R.; Rassat, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 180.
13. Kanno, F.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1993, 115, 847.
14. Borden, W. T.; Iwamura, H.; Berson, J. A. Acc. Chem. Res. 1994, 27, 109.
15. Tukada, H.; Mutai, K.; Iwamura, H. Chem. Commun. 1987, 1159.
16. Matsuda, K.; Iwamura, H. Chem. Commun. 1996, 1131-1132.
17. Esat, B.; Walton, R.; Lahti, P. M. J. Am. Chem. Soc. 1998, 120, 5122.
18. Forrester, A. R.; Hay, J. M.; Thomson, R. H. Organic Chemistry of Stable Free Radicals; Academic Press: New York, 1968.
19. Altwicker, E. R. Chem. Rev. 1967, 67, 475.
20. Satoh, Y.; Shi, C. Synthesis 1994, 1146.
21. Duling, D. R. J. Magn. Reson. 1994, B104, 105.
22. Kirste, B. Anal. Chim. Acta 1992, 265, 191.
23. Teki, Y.; Fujita, I.; Takui, T.; Kinoshita, T.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 11499.
24. Minato, M.; Lahti, P. M. J. Phys. Org. Chem. 1991, 4, 459.
25. Stewart, J. J. P. J. Comput.-Aided Mol. Des. 1990, 4, 1.
26. Lahti, P. M.; Ichimura, A. S.; Berson, J. A. J. Org. Chem. 1989, 54, 958.
27. Lahti, P. M.; Ichimura, A. S. J. Org. Chem. 1991, 56, 3030.
28. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209, 221.
29. Avdievich, N. I.; Forbes, M. D. E. J. Phys. Chem. 1996, 100, 1993.
30. Avdievich, N. I.; Forbes, M. D. E. J. Phys. Chem. 1995, 99, 9660.
31. Shultz, D. A.; Farmer, G. T. J. Org. Chem. 1998, 63, 6254.
32. Stowell, J. C. J. Org. Chem. 1971, 36, 3055.
33. For a preparation of 4-bromo-2,6-di-tert-butylanisole, see Dhami, K. S.; Stothers, J.B. Can. J. Chem. 1986, 44, 2855.
34. 2 was prepared by addition of lead tetraacetate to distilled water, filtration, washing of the product with distilled water to neutral pH, and drying in air to give a very dark brown powder of suitable quality for oxidation.