Generation, isolation, and reactivity of a kinetically stabilized diphosphene anion radical

Journal of Organometallic Chemistry

Volumn 693, Issue 4, 2008, Pages 625-632

  Nagahora, Noriyoshi ^a   Sasamori, Takahiro ^a   Hosoi, Yoshinobu ^b   Furukawa, Yukio ^b   Tokitoh, Norihiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b WASEDA UNIVERSITY   (Japan)

Author keywords

Anion radical; Cyclic voltammetry; Diphosphene; ESR spectrum; Reduction; UV Vis spectrum

Indexed keywords

CHALCOGENIDES; CYCLIC VOLTAMMETRY; ELECTRON SPIN RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ULTRAVIOLET SPECTROSCOPY;

ANION RADICALS; CHALCOGENATION REACTIONS; DIPHOSPHENE; ONE-ELECTRON REDUCTION;

FREE RADICALS;

EID: 39049109087     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2007.10.061     Document Type: Article

References (62)

1. Cowley A.H., Kilduff J.E., Lasch J.G., Mehrotra S.K., Norman N.C., Pakulski M., Whittlesey B.R., Atwood J.L., and Hunter W.E. Inorg. Chem. 23 (1984) 2582
2. Weber L. Chem. Rev. 92 (1992) 1839
3. Power P.P. Chem. Rev. 99 (1999) 3463
4. Tokitoh N. J. Organomet. Chem. 611 (2000) 217
5. Yoshifuji M., Shima I., Inamoto N., Hirotsu K., and Higuchi T. J. Am. Chem. Soc. 103 (1981) 4587
6. Gleiter R., Friedrich G., Yoshifuji M., Shibayama K., and Inamoto N. Chem. Lett. 13 (1984) 313
7. Yoshifuji M., Hashida T., Inamoto N., Hirotsu K., Horiuchi T., Higuchi T., Ito K., and Nagase S. Angew. Chem., Int. Ed. Engl. 24 (1985) 211
8. Allen T.L., Scheiner A.C., Yamaguchi Y., and Schaefer H.F. J. Am. Chem. Soc. 108 (1986) 7579
9. Ito K., and Nagase S. Chem. Phys. Lett. 126 (1986) 531
10. Nagase S., Suzuki S., and Kurakake T. J. Chem. Soc., Chem. Commun. (1990) 1724
11. Cotton F.A., Cowley A.H., and Feng X. J. Am. Chem. Soc. 120 (1998) 1795
12. Çetinkaya B., Hudson A., Lappert M.F., and Goldwhite H. J. Chem. Soc., Chem. Commun. (1982) 609
13. Çetinkaya B., Hitchcock P.B., Lappert M.L., Thorne A.J., and Goldwhite H. J. Chem. Soc., Chem. Commun. (1982) 691
14. Bard A.J., Cowley A.H., Kilduff J.E., Leland J.K., Norman N.C., Pakulski M., and Heath G.A. J. Chem. Soc., Dalton Trans. (1987) 249
15. Culcasi M., Gronchi G., Escudié J., Couret C., Pujol L., and Tordo P. J. Am. Chem. Soc. 108 (1986) 3130
16. Shah S., Burdette S.C., Swavey S., Urbach F.L., and Protasiewicz J.D. Organometallics 16 (1997) 3395
17. Binder H., Riegel B., Heckmann G., Moscherosch M., Schnering H.-G.v., Hönle W., Flad H.-J., and Savin A. Inorg. Chem. 35 (1996) 2119
18. Geier J., Harmer J., and Grützmacher H. Angew. Chem., Int. Ed. 43 (2004) 4093
19. An ESR spectrum of an anion radical of asymmetric diaryldiphosphenes was also reported, see. Dutan C., Shah S., Smith R.C., Choua S., Berclaz T., Geoffroy M., and Protasiewicz J.D. Inorg. Chem. 42 (2003) 6241
20. Tokitoh N., Arai Y., Okazaki R., and Nagase S. Science 277 (1997) 78
21. Tokitoh N., Arai Y., Sasamori T., Okazaki R., Nagase S., Uekusa H., and Ohashi Y. J. Am. Chem. Soc. 120 (1998) 433
22. Sasamori T., Takeda N., and Tokitoh N. Chem. Commun. (2000) 1353
23. Sasamori T., Arai Y., Takeda N., Okazaki R., Furukawa Y., Kimura M., Nagase S., and Tokitoh N. Bull. Chem. Soc. Jpn. 75 (2002) 661
24. Sasamori T., Takeda N., Fujio M., Kimura M., Nagase S., and Tokitoh N. Angew. Chem., Int. Ed. 41 (2002) 139
25. Sasamori T., Takeda N., and Tokitoh N. J. Phys. Org. Chem. 16 (2003) 450
26. Sasamori T., Mieda E., Takeda N., and Tokitoh N. Chem. Lett. 33 (2004) 104
27. Nagahora N., Sasamori T., Takeda N., and Tokitoh N. Chem. Eur. J. 10 (2004) 6146
28. Sasamori T., Mieda E., Nagahora N., Takeda N., Takagi N., Nagase S., and Tokitoh N. Chem. Lett. 34 (2005) 166
29. Sasamori T., Mieda E., Takeda N., and Tokitoh N. Angew. Chem., Int. Ed. 44 (2005) 3717
30. Nagahora N., Sasamori T., and Tokitoh N. Chem. Lett. 35 (2006) 220
31. Sasamori T., Mieda E., Nagahora N., Sato K., Shiomi D., Takui T., Hosoi Y., Furukawa Y., Takagi N., Nagase S., and Tokitoh N. J. Am. Chem. Soc. 128 (2006) 12582
32. Sasamori T., Tsurusaki A., Nagahora N., Matsuda K., Kanemitsu Y., Watanabe Y., Furukawa Y., and Tokitoh N. Chem. Lett. 35 (2006) 1382
33. Izutsu K. Electrochemistry in Nonaqueous Solutions (2002), Wiley-VCH, Weinheim
34. 6 in the presence of 18-crown-6 as an internal standard.
35. Gynane M.J.S., Hudson A., Lappert M.F., Power P.P., and Goldwhite H. J. Chem. Soc., Chem. Commun. (1976) 623
36. Gynane M.J.S., Hudson A., Lappert M.F., Power P.P., and Goldwhite H. Dalton Trans. (1980) 2428
37. Power P.P. Chem. Rev. 103 (2003) 789
38. Yoshifuji M., Shibayama K., Inamoto N., and Watanabe T. Chem. Lett. 12 (1983) 585
39. Loss S., Magistrato M., Cataldo L., Hoffmann S., Geoffroy M., Röthlisberger U., and Grützmacher H. Angew. Chem., Int. Ed. 40 (2001) 723
40. Hassler K., and Hofler F. Z. Anorg. Allg. Chem. 443 (1978) 125
41. Baudler M., and Glinka K. Chem. Rev. 93 (1993) 1623
42. Some alkyl halides are known to be as weak one-electron oxidants, see. Connelly N.G., and Geiger W.E. Chem. Rev. 96 (1996) 877
43. Baudler M., Suchomel H., Fürstenberg G., and Schings U. Angew. Chem. 93 (1981) 1087
44. Yoshifuji M., Ando K., Shibayama K., Inamoto N., Hirotsu K., and Higuchi T. Angew. Chem., Int. Ed. Engl. 22 (1983) 418
45. Yoshifuji M., Shibayama K., Inamoto N., Hirotsu K., and Higuchi T. J. Chem. Soc., Chem. Commun. (1983) 862
46. Niecke E., and Rüger R. Angew. Chem. 95 (1983) 154
47. Weber L., Meine G., Boese R., and Niederprüm N. Z. Naturforsch 43b (1988) 715
48. * with elemental sulfur in triethylamine at 70 °C for 2 h gave the corresponding diphosphene sulfide in 67% yield. The thermal or photochemical reactions of the diphosphene sulfide quantitatively afforded the corresponding thiadiphosphirane.
49. 6 at 120 °C for 164 h in the presence of triethylamine afforded the corresponding thiadiphosphirane in 57% yield.
50. 6 at 120 °C for 12 h in the presence of triethylamine gave the corresponding thiadiphosphirane in 59% yield.
51. Diphosphenes TbtP{double bond, long}PTbt (1) and BbtP{double bond, long}PBbt are inert toward elemental sulfur in THF at room temperature.
52. Yoshifuji M., Shibayama K., and Inamoto N. Chem. Lett. 13 (1984) 603
53. Jutzi P., Brusdeilins N., Stammler H.-G., and Neumann B. Chem. Ber. 127 (1994) 997
54. Jochem G., Karaghiosoff K., Plank S., Dick S., and Schmidpeter A. Chem. Ber. 128 (1995) 1207
55. Voelker H., Pieper U., Roesky H.W., and Sheldrick G.M. Z. Naturforsch 49b (1994) 255
56. * with elemental selenium in triethylamine at 70 °C for 2 h gave the corresponding selenadiphosphirane in 14% yield; see Ref. [20a].
57. 6 at 120 °C for 120 h in the presence of triethylamine gave the corresponding selenadiphosphirane in 57% yield; see Ref. [7f].
58. Pangborn A.B., Giardello M.A., Grubbs R.H., Rosen R.K., and Timmers F.J. Organometallics 15 (1996) 1518
59. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, gaussian 03, Revision B.05, Gaussian, Inc., Pittsburgh, PA, 2003.
60. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
61. Becke A.D. Phys. Rev. A 38 (1988) 3098
62. Becke A.D. J. Chem. Phys. 98 (1993) 5648