Browse > Article
http://dx.doi.org/10.5012/bkcs.2010.31.12.3745

Palladium(II) p-Tolylamide and Reaction with CO2 to Generate a Carbamato Derivative  

Seul, Jung-Min (Department of Chemistry, Dongguk University)
Park, Soon-Heum (Department of Chemistry, Dongguk University)
Publication Information
Abstract
Pd(II) p-tolylamide Pd(2,6-$(Ph_2PCH_2)_2C_6H_3$)(NH($C_6H_4Me$-p)) (1) was metathetically prepared by the reaction of Pd(2,6-$(Ph_2PCH_2)_2C_6H_3$)Cl with NaNH($C_6H_4Me$-p). Treatment of 1 with carbon dioxide affords the palladium(II) carbamate Pd(2,6-$(Ph_2PCH_2)_2C_6H_3$)(OC(O)NH($C_6H_4Me$-p)) (2), quantitatively. Complex 2 reacts with HX (X = Cl, OTf) to give Pd(2,6-$(Ph_2PCH_2)_2C_6H_3$)X, $NH_2$(p-Tol) and $CO_2$. Reaction of the palladium(II) carbamate with MeI produced Pd(2,6-$(Ph_2PCH_2)_2C_6H_3$)I along with generation of methyl N-tolylcarbamate MeOC(O)NH($C_6H_4Me$-p), exclusively.
Keywords
Palladium arylamide; Palladium carbamate; Insertion of $CO_2$; Methyl N-aryl carbamate;
Citations & Related Records

Times Cited By Web Of Science : 1  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
  • Reference
1 Bacchi, A.; Dell’Amico, D. B.; Calderazzo, F.; Giurlani, U.; Pelizzi, G.; Rocchi, L. Gazz. Chim. Ital. 1992, 122, 429.
2 Dell’Amico, D. B.; Calderazzo, F.; Labella, L.; Maichle-Mossmer, C.; Strahle, J. J. Chem. Soc., Chem. Commun. 1994, 1555.
3 Abram, U.; Dell’Amico, D. B.; Calderazzo, F.; Kaskel, S.; Labella, L.; Marchetti, F.; Rovai, R.; Strahle, J. Chem. Commun. 1997, 1941.
4 Dell’Amico, D. B.; Calderazzo, F.; Marchetti, F.; Perego, G. J. Chem. Soc., Dalton Trans. 1983, 483.
5 Dell’Amico, D. B.; Calderazzo, F.; Giurlani, U.; Pelizzi, G. Chem. Ber. 1987, 120, 955.   DOI
6 Abis, L.; Dell’Amico, D. B.; Busetto, C.; Calderazzo, F.; Caminiti, R.; Ciofi, C.; Garbassi, F.; Masciarelli, G. J. Mater. Chem. 1998, 8, 751.   DOI   ScienceOn
7 Abis, L.; Dell'Amico, D. B.; Busetto, C.; Calderazzo, F.; Caminiti, R.; Garbassi, F.; Tomei, A. J. Mater. Chem. 1998, 8, 2855.   DOI   ScienceOn
8 Rimml, H.; Venanzi, L. M. J. Organomet. Chem. 1983, 259, C6. 11.
9 Boncella, J. M.; Villanueva, L. A. J.Organomet. Chem. 1994, 465, 297.   DOI   ScienceOn
10 Boncella, J. M.; Eve, T. M.; Rickman, B.; Abboud, K. Polyhedron 1998, 17, 725.   DOI   ScienceOn
11 Glueck, D. S.; Winslow, L. J.; Bergman, R. G. Organometallics 1991, 10, 1462.   DOI
12 Alessio, R.; Dell’Amico, D. B.; Calderazzo, F.; Englert, U.; Guarini, A.; Labella, L.; Strasser, P. Helv. Chim. Acta 1998, 81, 219.   DOI   ScienceOn
13 Alessio, R.; Dell'Amico, D. B.; Calderazzo, F.; Englert, U. Gazz. Chim. Ital. 1993, 123, 719.
14 Seligson, A. L.; Cowan, R. L.; Trogler, W. C. Inorg. Chem. 1991, 30, 3371.   DOI
15 Ruiz, J.; Martnez, M. T.; Florenciano, F.; Rodrguez, V.; Lopez, G.; Prez, J.; Chaloner, P. A.; Hitchcock, P. B. Inorg. Chem. 2003, 42, 3650.
16 Mandal, S. K.; Ho, D. M.; Orchin, M. Organometallics 1993, 12, 1714.   DOI   ScienceOn
17 Hevia, E.; Perez, J.; Riera, L.; Riera, V.; delRio, I.; Garcia-Granda, S.; Miguel, D. Chem. Eur. J. 2002, 8, 4510.   DOI   ScienceOn
18 Ryu, S. Y.; Kim, H.; Kim, H. S.; Park, S. J. Organomet. Chem. 1999, 592, 194.   DOI   ScienceOn
19 Ryu, S. Y.; Yang, W.; Kim, H. S.; Park, S. Bull. Korean Chem. Soc. 1997, 18, 1183.
20 Seul, J. M.; Park, S. J. Chem. Soc. Dalton Trans. 2002, 1153.
21 Verkade, J. G. Chem. Rev. 1972, 9, 1.
22 Pregosin, P. S.; Kunz, R. Helv. Chim. Acta 1975, 58, 423.   DOI
23 Verstuyft, A. W.; Nelson, J. H.; Cary, L. W. Inorg. Chem. 1976, 15, 732.   DOI
24 Pregosin, P. S.; Kunz, R. W. 31P- and 13C-NMR of Transition Metal Phosphine Complexes; Springer: Berlin, 1979; p 65.
25 Aresta, M.; Dibenedetto, A. Dalton Trans. 2007, 28, 2975.
26 Walther, D.; Geßler, S.;Ritter, U.; Schmidt, A.; Hamza, K.; Görls, H.; Sieler, J. Chem. Ber.1995, 128, 281.   DOI
27 Mahe, R.; Sasaki, Y.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1989, 54, 1518.   DOI
28 McGhee, W. D.; Riley, D. P. Organometallics 1992, 11, 900.   DOI
29 Aresta, M.; Dibenedetto, A.; Quaranta, E. J.Chem. Soc. Dalton Trans. 1995, 3359.
30 Sneeden, R. P. A. In Comprehensive Organometallic Chemistry; Vol. 8, Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: New York, 1982; chapter 50.4, p 225.
31 Leitner, W. Coord. Chem. Rev. 1996, 153, 257.   DOI   ScienceOn
32 Pandey, K. K. Coord. Chem.Rev. 1995, 140, 37.   DOI   ScienceOn
33 Yin, X.; Moss, J. R. Coord. Chem. Rev. 1999, 181, 27.   DOI   ScienceOn
34 Ozawa, F.; Ito, T.; Yamamoto, A. Chem. Lett. 1979, 735.
35 Anillo, A.; Dell'Amico, D. B.; Calderazzo, F.; Nardelli, M.; Pelizzi, G.; Rocchi, L. J. Chem. Soc., Dalton Trans. 1991, 2845.
36 Abram, U.; Dell'Amico, D. B.; Calderazzo, F.; Marchetti, L.; Strähle, J. J. Chem. Soc., Dalton Trans. 1999, 4093.
37 Belforte, A.; Dell'Amico, D. B.; Calderazzo, F. Chem. Ber. 1988, 121, 1891.   DOI
38 Srivastava, R. S.; Singh, G.; Nakano, M.; Osakada, K.; Ozawa, F.; Yamamoto, A. J. Organomet. Chem. 1993, 451, 221.   DOI   ScienceOn
39 Cowan, R. L.; Trogler, W. C. J. Am. Chem. Soc. 1989, 111, 4750.   DOI
40 Park, S.; Rheingold, A. L.; Roundhill, D. M. Organometallics 1991, 10, 615.   DOI
41 Gabriele, B.;Salerno, G.; Mancuso, R.; Costa, M. J. Org. Chem. 2004, 69, 4741.   DOI   ScienceOn
42 Sakakura, T.; Choi, J. C.; Yasuda, H. Chem. Rev. 2007, 107,2365.   DOI   ScienceOn
43 McGhee, W. D.; Riley, D. P.; Christ, M. E.; Christ, K. M. Organometallics 1993, 12, .1429   DOI   ScienceOn
44 Fournier, J.; Bruneau,C.; Dixneuf, P. H.; Lecolier, S. J. Org. Chem. 1991, 56, 4456.   DOI
45 Aresta, M.; Quaranta, E. ChemTech 1997, 27, 32.