Electrophilic Additions to Diphosphenes (RP=PR)

Journal of the American Chemical Society

Volumn 105, Issue 14, 1983, Pages 4845-4846

  Cowley, A H ^a   Kilduff, J E ^a   Norman, N C ^a   Pakulski, M ^a   Atwood, J L ^b   Hunter, W E ^b  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845552297     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00352a059     Document Type: Article

References (8)

1. (a) West, R.; Fink, M. J.; Michl, J. Science (Washington, D.C.) 1981, 214, 1343. (b) Masamune, S.; Hanzawa, Y.; Murakami, S.; Bally, T.; Blount, J. F. J. Am. Chem. Soc 1982, 104, 1150. (c) Boudjouk, P.; Han, B.-H.; Anderson, K. R. J. Am. Chem. Soc. 1982, 104, 4992.
2. Masamune, S.; Hanzawa, Y.; Williams, D. J. J. Am. Chem. Soc. 1982, 104, 6136.
3. For a discussion of the bonding in the [(Me3Si)2CH]2 Sn, see: Fjeldberg, T.; Haaland, A.; Lappert, M. F.; Schilling, B. E. R.; Seip, R.; Thorne, A. J. J. Chem. Soc, Chem. Commun. 1982, 1407, and references therein.
4. (a) Yoshifuji, M.; Shima, I.; Inamoto, N.; Hirotsu, K.; Higuchi, T. J. Am. Chem. Soc. 1981, 103, 4587. (b) Cowley, A. H.; Kilduff, J. E.; Newman, T. H.; Pakulski, M. J. Am. Chem. Soc. 1982, 104, 5820. (c) Bertrand, G.; Couret, C.; Escudie, J.; Majid, S.; Majoral, J.-P. Tetrahedron Lett. 1982, 23, 3567. (d) Cetinkaya, B.; Hudson, A.; Lappert, M. F.; Goldwhite, H. J. J. Chem. Soc, Chem. Commun. 1982, 609. (e) Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J.; Goldwhite, H. J. Chem. Soc, Chem. Commun. 1982, 691, (f) Couret, C.; Escudie, J.; Satge, J. Tetrahedron Lett. 1982, 23, 4941.
5. For a preliminary account of the reactivity of (mes)2Sl=Si(mes)2(mes = mesityl) see: Fink, M. J.; De Young, D. J.; West, R.; Michl, J. J. Am. Chem. Soc 1983, 105, 1070.
6. the only exception is when R=CF3 (Dobbie, R. C.; Goshij, P. D.; Straughan, B. P. J. Chem. Soc, Dalton Trans. 1975, 2368) or when RP-(H)(halogen) is coordinated to a transition metal: Marinetti, A.; Mathey, F. Organometallics 1982, 1, 1488 and references therein.
7. Previously we have demonstrated that two-coordinate phosphenium cations undergo C-H oxidative addition reactions. See: (a) Cowley, A. H.; Kemp, R. A.; Stewart, C. A. J. Am. Chem. Soc. 1982, 104, 3239. (b) Cowley, A. H.; Mehrotra, S. K. J. Am. Chem. Soc. 1983, 105, 2074. (c) Baceiredo, A.; Bertrand, G.; Mazerolles, P.; Majoral, J.-P. J. Chem. Soc, Chem. Commun. 1981, 1197. (d) Yoshifuji M.; Shima, I.; Ando, K.; Inamoto, N. Tetrahedron Lett. 1983, 24, 933.
8. After the submission of this paper two reports on the reactivity of diphosphenes have appeared: (a) Niecke, E.; Rüger, R. Angew Chem., Int. Ed. Engl. 1983, 22, 155. (b) Yoshifuji, M.; Ando, K.; Toyota, K.; Shima, I.; Inamoto, N. J. Chem. Soc, Chem. Commun. 1983, 419.