Abstract
The reaction of benzylaminate CN-palladacycle with chlorine dioxide was found to produce the 3-chlorine-substituted analog through the formal insertion of chlorine into the Pd-C bond followed by repeated ortho-palladation of the modified ligand. The structure of the resulting dimeric complex was confirmed by X-ray diffraction study of its triphenylphosphine derivative. A comparison of the 1H NMR spectra of the phosphine adducts of the starting and chlorinated complexes shows high conformational stability of the new palladacycle. Advantages of the new route to conformational stabilization of labile palladacycles are discussed.
Similar content being viewed by others
References
A. D. Ryabov, Usp. Khim., 1985, 54, 253 [Russ. Chem. Rev., 1985, 54 (Engl. Transl.)].
M. Pfeffer, Recl. Trav. Chim. Pays-Bas, 1990, 109, 567.
Ch. R. Sinha, D. Bandyopadhyay, and A. Chakravorty, J. Chem. Soc., Chem. Commun., 1988, 468.
B. A. Grigor and A. J. Nielson, J. Organomet. Chem., 1977, 129, C17.
A. K. Mahapatra, D. Bandyopadhyay, P. Bandyopadhyay, and A. Chakravorty, J. Chem. Soc., Chem. Commun., 1984, 999.
A. K. Mahapatra, D. Bandyopadhyay, P. Bandyopadhyay, and A. Chakravorty, Inorg. Chem., 1986, 25, 2214.
Ch. Sinha, D. Bandyopadhyay, and A. Chakravorty, Inorg. Chem., 1988, 27, 1173.
Ch. Kumar, P. S. Chattopadhayay, Ch. Sinha, and A. Chakravorty, J. Organomet. Chem., 1992, 439, 91.
K. Kamaraj and D. Bandyopadhyay, J. Am. Chem. Soc, 1997, 119, 8099.
J. E. Baldwin, C. Najera, and M. Yus, J. Chem. Soc., Chem. Commun., 1985, 126.
P. L. Alsters, H. T. Teunissen, J. Boersma, and G. van Koten, Recl. Trav. Chim. Pays-Bas, 1990, 109, 487.
P. L. Alsters, H. T. Teunissen, J. Boersma, A. L. Spek, and G. van Koten, Organometallics, 1993, 12, 4691.
P. L. Alsters, J. Boersma, and G. van Koten, Tetrahedron Lett, 1991, 32, 675.
P. L. Alsters, J. Boersma, and G. van Koten, Organometallics, 1993, 12, 1629.
R. Bhawmick, H. Biswas, P. Bandyopadhyay, and A. Chakravorty, J. Organomet. Chem., 1995, 498, 81.
K. Kamaraj and D. Bandyopadhyay, Organometallics, 1999, 18, 438.
D. R. Fahey, J. Organomet. Chem., 1970, 27, 283.
H. B. Kagan, in Asymmertic Synthesis, Ed. J. D. Morrison, Academic Press, Inc., London, 1985, 5, 1.
V. V. Dunina and I. P. Beletskaya, Zh. Org. Khim., 1992, 28, 2369 [Russ. J. Org. Chem., 1992, 28 (Engl. Transl.)].
S. T. Handy, Current Organic Chemistry, 2000, 4, 363.
R. P. Wayne, G. Poulet, P. Biggs, J. P. Burrows, R. A. Cox, P. J. Crutzen, G. D. Hayman, M. E. Jenkin, G. Le Bras, G. K. Moortgat, U. Platt, and R. N. Schindler, Atmos. Environ, 1995, 29, 2677.
A. V. Kuchin, L. L. Frolova, and I. V. Dreval’, Izv. Akad. Nauk, Ser. Khim., 1996, 1871 [Russ. Chem. Bull., 1996, 45, 1781 (Engl. Transl.)].
A. V. Kuchin, S. A. Rubtsova, L. P. Karmanova, S. N. Subbotina, and I. V. Loginova, Izv. Akad. Nauk, Ser. Khim., 1998, 2110 [Russ. Chem. Bull., 1998, 47, 2051 (Engl. Transl.)].
A. V. Kuchin, S. A. Rubtsova, I. V. Loginova, and S. N. Subbotina, Zh. Org. Khim., 2000, 36, 1819 [Russ. J. Org. Chem., 2000, 36 (Engl. Transl.)].
A. V. Kuchin, S. A. Rubtsova, and I. V. Loginova, Izv. Akad. Nauk, Ser. Khim., 2001, 413 [Russ. Chem. Bull., Int. Ed., 2001, 50, 432].
O. M. Lezina, S. A. Rubtsova, and A. V. Kuchin, Izv. Akad. Nauk, Ser. Khim., 2003, 1779 [Russ. Chem. Bull., Int. Ed., 2003, 52, 1877].
A. V. Kuchin and L. L. Frolova, Izv. Akad. Nauk, Ser. Khim., 2000, 1658 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1647].
A. V. Kuchin, I. A. Dvornikova, and I. Yu. Nalimova, Izv. Akad. Nauk, Ser. Khim., 1999, 2025 [Russ. Chem. Bull., 1999, 48 (Engl. Transl.)].
U. Glabisz, J. Chem. Soc., Sect. A, 1966, 211.
J. Jalowiczor, Zesz. Nauk. Politech. Szczecin., Chem., 1968, 8, 105.
B. O. Lindgren and B. Ericsson, Acta Chem. Scand., 1969, 23, 3451.
W. J. Masschelein, Chlorine Dioxide: Chemistry and Environmental Impact of Oxychlorine Compounds, Ann Arbor: Ann Arbor Publishers, Inc., 1979, 418 p.
B. O. Lindgren and H. T. Nilsson, Acta Chem. Scand., Ser. B, 1974, 847.
C. Rav-Acha, Water Res., 1984, 18, 1329.
A. V. Kutchin, I. A. Dvornikova, I. Yu. Chukicheva, L. L. Frolova, V. V. Dunina, and O. N. Gorunova, Book of Abstracts of XX th International Conference on Organometallic Chemistry (Corfu-Greece, 7–12 July, 2002), Corfu, 2002, P37.
J. E. Baldwin, R. H. Jones, C. Najera, and M. Yus, Tetrahedron, 1985, 41, 699.
L. V. Desai, K. L. Hull, and M. S. Sanford, J. Am. Chem. Soc., 2004, 126, 9542.
J. Albert, J. Granell, and J. Sales, Polyhedron, 1989, 8, 2725.
J. A. C. Allison, H. S. El Khadem, and C. A. Wilson, J. Heterocycl. Chem., 1975, 12, 1275.
D. R. Fahey, J. Chem. Soc., Chem. Commun., 1970, 417.
Ph. J. Reid, Acc. Chem. Res., 2001, 34, 691.
J. Albert, M. Gomes, J. Granell, J. Sales, and X. Solans, Organometallics, 1990, 9, 1405.
V. V. Dunina, M. Yu. Kazakova, Yu. K. Grishin, O. R. Malyshev, and E. I. Kazakova, Izv. Akad. Nauk, Ser. Khim., 1997, 1375 [Russ. Chem. Bull., 1997, 46, 1321 (Engl. Transl.)].
V. V. Dunina, L. G. Kuz’mina, M. Yu. Kazakova, O. N. Gorunova, Yu. K. Grishin, and E. I. Kazakova, Eur. J. Inorg. Chem., 1999, 1029.
V. V. Dunina, O. N. Gorunova, E. B. Averina, Yu. K. Grishin, L. G. Kuz’mina, and J. A. K. Howard, J. Organomet. Chem., 2000, 603, 138.
H. Günter, NMR Spectroscopy. An Introduction, J. Wiley and Sons, Chichester-New York-Brisbane-Toronto, 1980.
N. N. Alcock, J. M. Brown, and D. J. Hulmes, Tetrahedron: Asymmetry, 1993, 4, 743.
N. N. Alcock, D. J. Hulmes, and J. M. Brown, J. Chem. Soc., Chem. Commun., 1995, 395.
B. W. Skelton, G. F. Swiegers, A. H. White, and S. B. Wild, Austral. J. Chem., 1998, 51, 1141.
W. McFarlane, J. D. Swarbrick, and J. L. Bookham, J. Chem. Soc., Dalton Trans., 1998, 3233.
D. C. R. Hockless, R. C. Mayadunne, and S. B. Wild, Tetrahedron: Asymmetry, 1995, 6, 3031.
B. H. Aw, S. Selvaratnam, P.-H. Leung, N. H. Rees, and W. McFarlane, Tetrahedron: Asymmetry, 1996, 7, 1753.
S. B. Wild, Coord. Chem. Revs, 1997, 166, 291.
S. Otsuka, A. Nakamura, T. Kano, and K. Tani, J. Am. Chem. Soc., 1971, 93, 4301.
L. G. Kuz’mina, Yu. T. Struchkov, O. A. Zalevskaya, V. V. Dunina, and V. M. Potapov, Zh. Obshch. Khim., 1987, 57, 2499 [J. Gen. Chem. USSR, 1987, 57 (Engl. Transl.)].
R. H. Contreras and J. E. Peralta, Prog. NMR Spectrosc., 2000, 37, 321.
P. W. Clark and S. F. Dyke, J. Organomet. Chem., 1984, 276, 421.
Y. Fuchita, H. Tsuchiya, and A. Miyafuji, Inorg. Chim. Acta, 1995, 233, 91.
V. V. Dunina, N. S. Gulyukina, I. V. Byakova, Yu. F. Oprunenko, and I. P. Beletskaya, Zh. Org. Khim., 1994, 30, 1497 [Russ. J. Org. Chem., 1994, 30 (Engl. Transl.)].
K. Tani, H. Tashiro, M. Yoshida, and Ts. Yamagata, J. Organomet. Chem., 1994, 469, 229.
A. Bondi, J. Phys. Chem., 1964, 68, 441.
O. N. Gorunova, Yu. K. Grishin, A. V. Churakov, L. G. Kuz’mina A. V. Kutchin, and V. V. Dunina, Book of Abstracts of International Conference “Modern Trends in Organo-element and Polymer Chemistry” (Moscow, 2004, May 30–June 4), Moscow, 2004, 92.
R. P. Polniaszek and C. R. Kaufman, J. Am. Chem. Soc., 1989, 111, 4859.
Y. Li, S. Selvaratnam, J. J. Vittal, and P.-H. Leung, Inorg. Chem., 2003, 42, 3229.
Y. Li, Kh.-H. Ng, S. Selvaratnam, G.-Kh. Tan, J. J. Vittal, and P.-H. Leung, Organometallics, 2003, 22, 834.
J. T. Sharp, I. Gosney, and A. G. Rowley, Practical Organic Chemistry. A Student Handbook of Techniques. Chapman and Hall, London-New York, 1989.
T. A. Tumanova and I. E. Flis, Fiziko-khimicheskie osnovy otbelki [Physicochemical Fundamentals of Bleaching], Lesnaya prom-st’, Moscow, 1972, p. 236 (in Russian).
G. M. Sheldrick, Acta. Crystallogr., Sect. A, 1990, A46, 467.
G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, University of Gö ttingen, Göttingen, Germany, 1997.
Author information
Authors and Affiliations
Additional information
Dedicated to Academician N. S. Zefirov on the occasion of his 70th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2010–2019, September, 2005.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2010–2019, September, 2005.
Rights and permissions
About this article
Cite this article
Dunina, V.V., Gorunova, O.N., Grishin, Y.K. et al. A new method for modification of CN-palladacycles. Russ Chem Bull 54, 2073–2082 (2005). https://doi.org/10.1007/s11172-006-0079-4
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0079-4