Synthesis of two novel para-extended bisaroxyls and characterization of their triplet spin states

Abstract

2′,3,3″,5,5′,5″-Hexa-tert -butyl-1,1′:4′,1″-terphenyl-4,4″-dioxyl 3c and 3,3q′,5,5q′-tetra-tert- butyl-1,1′:4′,1″:4″,1‴:4‴,1 q′-quinquephenyl-4,4q′-dioxyl 3e, obtained by oxidation of the corresponding biphenols 1c and 1e, show thermally excited triplet spin states.

References

1. J. S. Miller and A. J. Epstein, Angew. Chem., Int. Ed. Engl., 1994, 33, 385.
2. E. Müller, A. Schick and K. Scheffler, Chem. Ber., 1959, 92, 474.
3. A. Rieker and K. Scheffler, Liebigs Ann. Chem., 1965, 689, 78.
4. G. Kothe, K.-H. Denkel and W. Summernam, Angew. Chem., Int. Ed. Engl., 1970, 9, 906.
5. G. Kothe, E. Ohmes, J. Brickmann and H. Zimmermann, Angew. Chem., Int. Ed. Engl., 1971, 10, 938.
6. D. E. Seeger, P. M. Lahti, A. R. Rossi and J. A. Berson, J. Am. Chem. Soc., 1986, 108, 1251.
7. K. Mukai and N. Inagaki, Bull. Chem. Soc. Jpn., 1980, 53, 2695.
8. J. Zhou and A. Rieker, J. Chem. Soc., Perkin Trans. 2, 1997, 931.
9. A. Rebmann, J. Zhou, P. Schuler, H. B. Stegmann and A. Rieker, J. Chem. Res., (S), 1996, 318(M), 1996, 1765.
10. T. Mitsumori, N. Koga and H. Iwamura, J. Phys. Org. Chem., 1994, 7, 43.
11. W. Adam, H. M. Harrer, F. Kita, H.-G. Korth and W. M. Nau, J. Org. Chem., 1997, 62, 1419.
12. E. Wasserman, L. C. Snyder and W. A. Yager, J. Chem. Phys., 1964, 41, 1763.
13. M. Minato and P. M. Lahti, J. Am. Chem. Soc., 1997, 119, 2187.
14. B. Bleaney and K. D. Bowers, Proc. R. Soc., London, Ser. A, 1952, 214.