Abstract
The reduction of aryldichlorophosphines in organic solvents was studied by cyclic voltammetry, preparative electrolysis, and chemical reduction. The reaction of the electrochemically generated (2,2′-bipyridine)nickel(0) complexes with aryldichlorophosphines PhPCl2 and tippPCl2 (tipp is 2,4,6-triisopropylphenyl) proceeds through the formation of highly reactive organophosphorus intermediates, whose reactions with diphenylacetylene and hex-1-ene afford phosphirene and phosphirane heterocycles, respectively.
Similar content being viewed by others
References
Technology Vision 2020. The US Chemical Industry, American Chemical Society, 1996, 75 pp.
Studies in Inorganic Chemistry 20. Phosphorus. An Outline of its Chemistry, Biochemistry and Technology, 5th ed., Ed. D. E. C. Corbridge, Elsevier (Science B. V.), Amsterdam-Lausanne-New York-Oxford-Shannon-Tokyo, 1995, 1208 pp.
F. Mathey, Angew. Chem., Int. Ed. Engl., 2003, 42, 1578; F. Mathey, Angew. Chem., Int. Ed. Engl., 1987, 26, 275.
F. Mathey, N. H. Tran Huy, and A. Marinetti, Helv. Chim. Acta, 2001, 84, 2938.
K. Lammertsma and M. J. M. Vlaar, Eur. J. Org. Chem., 2002, 4, 1127.
A. Marinetti, F. Mathey, J. Fischer, and A. Mitschler, J. Chem. Soc., Chem. Commun., 1982, 667; A. Marinetti, F. Mathey, J. Fischer, and A. Mitschler, J. Am. Chem. Soc., 1982, 104, 4484.
A. T. Termaten, H. Aktas, M. Schakel, A. W. Ehlers, M. Lutz, A. L. Spek, and K. Lammertsma, Organometallics, 2003, 22, 1827; B. T. Sterenberg, K. A. Udachin, and A. J. Carty, Organometallics, 2001, 20, 4463; M. J. M. Vlaar, P. Valkier, F. J. J. De Kanter, M. Schakel, A. W. Ehlers, A. L. Spek, M. Lutz, and K. Lammertsma, Chem. Eur. J., 2001, 7, 3551.
S. Blaurock and E. Hey-Hawkins, Eur. J. Inorg. Chem., 2002, 11, 2975; A. T. Termaten, T. Nijbacker, M. Schakel, M. Lutz, A. L. Spek, and K. Lammertsma, Chem. Eur. J., 2003, 9, 2200; J. Sanchez-Nieves, B. T. Sterenberg, K. A. Udachin, and A. J. Carty, J. Am. Chem. Soc., 2003, 125, 2404; A. T. Termaten, T. Nijbacker, M. Schakel, M. Lutz, A. L. Spek, and K. Lammertsma, Organometallics, 2002, 21, 3196.
R. Melenkivitz, D. J. Mindiola, and G. L. Hillhouse, J. Am. Chem. Soc., 2002, 124, 3846.
R. Waterman and G. L. Hillhouse, J. Am. Chem. Soc., 2003, 125, 13350.
R. Waterman and G. L. Hillhouse, Organometallics, 2003, 22, 5182.
D. G. Yakhvarov, Yu. H. Budnikova, N. H. Tran Huy, L. Ricard, and F. Mathey, Organometallics, 2004, 23, 1961.
Yu. G. Budnikova, Usp. Khim., 2002, 71, 127 [Russ. Chem. Rev., 2002, 71, 111 (Engl. Transl.)]; Y. H. Budnikova, J. Perichon, D. G. Yakhvarov, Y. M. Kargin, and O. G. Sinyashin, J. Organomet. Chem., 2001, 630, 185.
D. G. Yakhvarov, Yu. G. Budnikova, and O. G. Sinyashin, Elektrokhim., 2003, 39, 1407 [Russ. J. Electrochem., 2003, 39, 1261 (Engl. Transl.)].
M. Troupel, Ann. Chim., 1986, 76, 151; Y. Rollin, M. Troupel, D. G. Tuck, and J. Perichon, J. Organomet. Chem., 1986, 303, 131; G. Meyer, Y. Rollin, and J. Perichon, J. Organomet. Chem., 1987, 333, 263; M. Durandetti, J. Y. Nedelec, and J. Perichon, J. Org. Chem., 1996, 61, 1748; Yu. H. Budnikova, D. G. Yakhvarov, and Yu. M. Kargin, Mendeleev Commun., 1997, 67; D. G. Yakhvarov, Yu. G. Budnikova, and O. G. Sinyashin, Izv. Akad. Nauk, Ser. Khim., 2003, 545 [Russ. Chem. Bull., Int. Ed., 2003, 52, 567].
Yu. G. Budnikova, D. G. Yakhvarov, V. I. Morozov, Yu. M. Kargin, A. V. Il’yasov, Yu. N. Vyakhireva, and O. G. Sinyashin, Zh. Obshch. Khim., 2002, 72, 184 [Russ. J. Gen. Chem., 2002, 72, 168 (Engl. Transl.)].
H. Matschiner and H. Tanneberg, Z. Chem., 1980, 20, 218.
R. E. Dessy, T. Chivers, and W. Kitching, J. Am. Chem. Soc., 1966, 88, 467.
H. P. Stritt and H. P. Latscha, Z. Anorg. Allg. Chem., 1986, 542, 167.
Yu. G. Budnikova, A. M. Yusupov, and Yu. M. Kargin, Zh. Obshch. Khim., 1994, 64, 1153 [Russ. J. Gen. Chem., 1994, 64 (Engl. Transl.)]; Yu. G. Budnikova, A. M. Yusupov, and Yu. M. Kargin, Zh. Obshch. Khim., 1995, 65, 1655 [Russ. J. Gen. Chem., 1995, 65 (Engl. Transl.)].
A. H. Cowley, J. E. Kilduff, J. G. Lasch, N. C. Norman, M. Pakulski, F. Ando, and T. C. Wright, J. Am. Chem. Soc., 1983, 105, 7751.
J. B. M. Wit, G. T. van Eijkel, M. Schakel, and K. Lammertsma, Tetrahedron, 2000, 56, 137.
H. Behrens and A. Muller, Z. Anorg. Allg. Chem., 1965, 341, 124.
S. D. Ittel, Inorg. Synth., 1990, 28, 98.
F. Mathey, Sci. Synth., 2002, 12, 705.
X. Li, D. Lei, M. Y. Chiang, and P. P. Gaspar, J. Am. Chem. Soc., 1992, 114, 8526.
R. C. Smith, S. Shah, and J. D. Protasiewicz, J. Organomet. Chem., 2002, 646, 255.
U. Schmidt, Angew. Chem., Int. Ed. Engl., 1975, 14, 523.
P. Koelle, G. Linti, H. Noeth, G. L. Wood, C. K. Narula, and R. T. Paine, Chem. Ber., 1988, 121, 871.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 901–907, May, 2007.
Rights and permissions
About this article
Cite this article
Yakhvarov, D.G., Hey-Hawkins, E., Kagirov, R.M. et al. Electrocatalytic reduction of aryldichlorophosphines with the (2,2′-bipyridine)nickel complexes. Russ Chem Bull 56, 935–942 (2007). https://doi.org/10.1007/s11172-007-0142-9
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-007-0142-9