Organometallics in water: Three-coordinate [Pt0(N,N-chelate)(η2-olefin)] complexes containing new chiral ligands based on α-D-mannose

Organometallics

Volumn 17, Issue 18, 1998, Pages 3832-3834

  Ferrara, Maria L ^a   Orabona, Ida ^a   Ruffo, Francesco ^a   Funicello, Maria ^b   Panunzi, Achille ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF BASILICATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001230508     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980350i     Document Type: Article

References (24)

1. For recent examples, see: (a) Nait Ajjou, A.; Alper, H. J. Am. Chem. Soc. 1998, 120, 1466. (b) Lynn, D. M.; Mohr, B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 1627.
2. For recent examples, see: (a) Nait Ajjou, A.; Alper, H. J. Am. Chem. Soc. 1998, 120, 1466. (b) Lynn, D. M.; Mohr, B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 1627.
3. Ligands based on carbohydrates are known. For recent examples, see: (a) Tanase, T.; Yasuda, Y.; Onaka, T.; Yano, S. J. Chem. Soc., Dalton Trans. 1998, 345 and references therein. (b) Stolmar, M.; Floriani, C.; Gervasio, G.; Viterbo, D. J. Chem. Soc., Dalton Trans. 1997, 1119. (c) Tschoerner, M.; Trabesinger, G.; Albinati, A.; Pregosin, P. S. Organometallics 1997, 16, 3447.
4. Ligands based on carbohydrates are known. For recent examples, see: (a) Tanase, T.; Yasuda, Y.; Onaka, T.; Yano, S. J. Chem. Soc., Dalton Trans. 1998, 345 and references therein. (b) Stolmar, M.; Floriani, C.; Gervasio, G.; Viterbo, D. J. Chem. Soc., Dalton Trans. 1997, 1119. (c) Tschoerner, M.; Trabesinger, G.; Albinati, A.; Pregosin, P. S. Organometallics 1997, 16, 3447.
5. Ligands based on carbohydrates are known. For recent examples, see: (a) Tanase, T.; Yasuda, Y.; Onaka, T.; Yano, S. J. Chem. Soc., Dalton Trans. 1998, 345 and references therein. (b) Stolmar, M.; Floriani, C.; Gervasio, G.; Viterbo, D. J. Chem. Soc., Dalton Trans. 1997, 1119. (c) Tschoerner, M.; Trabesinger, G.; Albinati, A.; Pregosin, P. S. Organometallics 1997, 16, 3447.
6. Horton, D.; Luetzow, A. E. Carbohydr. Res. 1968, 7, 101.
7. Compounds similar to 4 are known. For a recent example, see: Garcìa Fernàndez, J. M.; Mellet Ortiz, C.; Dìaz Pèrez, V. M.; Fuentes, J.; Kovàcs, J.; Pintèr, I. Tetrahedron Lett. 1997, 38, 4161.
8. P-C = 15 Hz, PPh(Me)Me′].
9. 8: C, 61.98; H, 5.82; N, 5.78. Found: C, 62.25; H, 5.74; N, 5.89.
10. Crascall, L. E.; Spencer, J. L. Inorg. Synth. 1990, 28, 126.
11. 12Pt: C, 45.20; H, 4.40; N, 3.40. Found: C, 45.18; H, 4.55; N, 3.26.
12. The NMR spectrum of the crude product displayed a small amount of aldehyde, while preliminary attempts to purify 1* resulted in extensive hydrolysis of the imine bond.
13. 9Pt: C, 37.80; H, 4.44; N, 4.41. Found: C, 37.93; H, 4.57; N, 4.27.
14. Water-soluble platinum(0) complexes are rare. For some recent examples, see: (a) Darensbourg, D. J.; Decuir, T. J.; Stafford, N. W.; Robertson, J. B.; Draper, J. D.; Reibenspies, J. H.; Kathò, A.; Joò, F. Inorg. Chem. 1997, 36, 4218. (b) Ellis, J. W.; Harrison, K. N.; Hoye, P. A. T.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. Inorg. Chem. 1992, 31, 3026.
15. Water-soluble platinum(0) complexes are rare. For some recent examples, see: (a) Darensbourg, D. J.; Decuir, T. J.; Stafford, N. W.; Robertson, J. B.; Draper, J. D.; Reibenspies, J. H.; Kathò, A.; Joò, F. Inorg. Chem. 1997, 36, 4218. (b) Ellis, J. W.; Harrison, K. N.; Hoye, P. A. T.; Orpen, A. G.; Pringle, P. G.; Smith, M. B. Inorg. Chem. 1992, 31, 3026.
16. 13C NMR spectra for the new complexes are reported in Tables S1-3 of the Supporting Information.
17. 2-(E)-NCCH= CHCN)]. Actually, the NMR spectrum of a fresh solution of the complex already disclosed significant amounts of both diastereomers.
18. Eliel, E. L. Stereochemistry of Carbon Compounds; McGraw-Hill: London, 1962; p 49.
19. Wicht, D. K.; Zhuravel, M. A.; Gregush, R. V.; Glueck, D. S.; Guzei, I. A.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1998, 17, 1412.
20. De Felice, V.; De Renzi, A.; Ruffo, F.; Tesauro, D. Inorg. Chim. Acta 1994, 219, 169.
21. Pt-H coupling constant of the imine proton in 5 points to the imine nitrogen atom being irons to oxygen. See: Albano, V. G.; Braga, D.; De Felice, V.; Panunzi, A.; Vitagliano, A. Organometallics 1987, 6, 517.
22. 3)].
23. 2O resulted in hydrolysis of one carboxymethyl group and formation of 6 within 12 h.
24. 1(β) takes place only in acidic solutions, while in neutral or alkaline media the anomeric carbon atoms are known to be configurationally stable.