p-Benzoquinone 2,3,5,6-tetrakis(diisopropyl phosphonate): A novel, highly bent p-Benzoquinone

Chemistry Letters

Volumn , Issue 7, 1999, Pages 633-634

  Kobiro, Kazuya ^a,b   Shi, Min ^a,c   Inoue, Yoshihisa ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b KOCHI UNIVERSITY OF TECHNOLOGY   (Japan)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033245496     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.633     Document Type: Article

References (19)

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3. F. Bickelhaupt and W. H. de Wolf, in "Advances in Strain in Organic Chemistry," JAL Press, Greenwich, CT, (1993), Vol. 3; V. V. Kane, W. H. de Wolf and F. Bickelhaupt, Tetrahedron, 50, 4575 (1994); Y. Tobe, Top. Curr. Chem., 172, 1 (1994).
4. See, Y. Tobe, S. Saiki, N. Utsumi, T. Kusumoto, H. Ishii, K. Kakiuchi, K. Kobiro and K. Naemura, J. Am. Chem. Soc., 118, 9488 (1996) and references cited therein.
5. See, R. S. Vagg, Acta Cryst., B33, 3708 (1977); M. D. Glick and L. F. Dahl, J. Organomet. Chem., 3, 200 (1965); G. G. Aleksandrov and Y. T. Struchkov, Zh. Strukt. Khim., 14, 1067 (1973); V. A. Uchtman and L. F. Dahl, J. Organomet. Chem., 40, 403 (1972); G. G. Aleksandrov and Y. T. Struchkov, Zh. Strukt. Khim., 12, 1037 (1971) and references cited therein.
6. See, R. S. Vagg, Acta Cryst., B33, 3708 (1977); M. D. Glick and L. F. Dahl, J. Organomet. Chem., 3, 200 (1965); G. G. Aleksandrov and Y. T. Struchkov, Zh. Strukt. Khim., 14, 1067 (1973); V. A. Uchtman and L. F. Dahl, J. Organomet. Chem., 40, 403 (1972); G. G. Aleksandrov and Y. T. Struchkov, Zh. Strukt. Khim., 12, 1037 (1971) and references cited therein.
7. See, R. S. Vagg, Acta Cryst., B33, 3708 (1977); M. D. Glick and L. F. Dahl, J. Organomet. Chem., 3, 200 (1965); G. G. Aleksandrov and Y. T. Struchkov, Zh. Strukt. Khim., 14, 1067 (1973); V. A. Uchtman and L. F. Dahl, J. Organomet. Chem., 40, 403 (1972); G. G. Aleksandrov and Y. T. Struchkov, Zh. Strukt. Khim., 12, 1037 (1971) and references cited therein.
8. See, R. S. Vagg, Acta Cryst., B33, 3708 (1977); M. D. Glick and L. F. Dahl, J. Organomet. Chem., 3, 200 (1965); G. G. Aleksandrov and Y. T. Struchkov, Zh. Strukt. Khim., 14, 1067 (1973); V. A. Uchtman and L. F. Dahl, J. Organomet. Chem., 40, 403 (1972); G. G. Aleksandrov and Y. T. Struchkov, Zh. Strukt. Khim., 12, 1037 (1971) and references cited therein.
9. See, R. S. Vagg, Acta Cryst., B33, 3708 (1977); M. D. Glick and L. F. Dahl, J. Organomet. Chem., 3, 200 (1965); G. G. Aleksandrov and Y. T. Struchkov, Zh. Strukt. Khim., 14, 1067 (1973); V. A. Uchtman and L. F. Dahl, J. Organomet. Chem., 40, 403 (1972); G. G. Aleksandrov and Y. T. Struchkov, Zh. Strukt. Khim., 12, 1037 (1971) and references cited therein.
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14. R. H. Thomson, in "The Chemistry of the Quinonoid Compounds, Part 1," ed by S. Patai, John Wiley, (1974), p 111; Y. Naruta and K. Maruyama, in "The Chemistry of the Quinonoid Compounds, Part 1," ed by S. Patai and Z. Rappoport, John Wiley, New York (1988), Vol. 2, p. 241.
15. T. Reetz, U. S. patent 2935518 (1960); Chem. Abstr, 54, 19598 (1960); F. Ramirez, E. H. Chen and S. Dershowitz, J. Am. Chem. Soc., 81, 4338 (1959).
16. T. Reetz, U. S. patent 2935518 (1960); Chem. Abstr, 54, 19598 (1960); F. Ramirez, E. H. Chen and S. Dershowitz, J. Am. Chem. Soc., 81, 4338 (1959).
17. -1, F(000)=408.00, 2Θmax = 55°, Mo Κα radiation, of 4912 reflections measured, 4677 were unique. The structure was solved by direct methods (SHELXS-86) and refined by full matrix least-squares method. The final R and Rw factors were 0.051 and 0.070 for 2346 reflections with I > 3.00 σ(I), respectively.
18. -1, F(000)=410.00, 2Θmax = 55°, Mo Κα radiation, of 5180 reflections measured, 4840 were unique. The structure was solved by direct methods (SHELXS-86) and refined with full matrix least-squares method. Hydrogen atom (H1) of hydroxyl group was found by difference synthesis. The final R and Rw factors were 0.049 and 0.086 for 3604 reflections with I > 3.00 σ(I), respectively.
19. Preliminary experiment of cyclic voltammogram measurements of 1 in acetonitrile showed that the first and the second reduction potentials are -0.196 and -0.970 V vs. SCE, respectively.