Restricted Rotation about the Metal-Aryl Bond in Platinum-Aryl Complexes of Chiral Diphosphines

Organometallics

Volumn 14, Issue 3, 1995, Pages 1195-1203

  Brown, John M ^a   Pérez Torrente, Jesús J ^a   Alcock, Nathaniel W ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000841775     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00003a021     Document Type: Article

References (32)

1. Brown, J. M.; Pérez-Torrente, J. J.; Alcock, N. W.; Clase, H. J. Organometallics 1995, 14, 207–213.
2. Miki, K.; Tanaka, M.; Kasai, N.; Wada, M. J. Organomet. Chem. 1988, 352, 385–396.
3. Griffiths, D. B.; Young, G. B. Organometallics 1986, 5, 1744–1746.
4. Alster, P. L.; Boersma, J.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Organometallics 1993, 12, 1639—1647.
5. Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031—1048 and references therein.
6. For recent examples of Pd aryls see: Kramer, R.; Polborn, K.; Beck, W. J. Organomet. Chem. 1992, 441, 333. Markies, B. A.; Canty, A. J.; Janssen, M. D.; Spek, A. L.; Boersma, J.; van Koten, G. Recl. Trav. Chim. Pays-Bas 1991, 110, 477-479; de Graaf, W.; van Wegen, J.; Boersma, J.; Spek, A. L.; van Koten, G. Recl. Trav. Chim. Pays-Bos 1989, 108, 275–277. Huser, M.; Youinou, M.-T.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1989, 28, 1386–1387.
7. Calhorda, M. J.; Brown, J. M.; Cooley, N. A. Organometallics 1991, 10, 1431–1439.
8. For recent examples of the X-ray structure of Pd acyls see: Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890-1895; Huang, L.; Ozawa, F.; Osakada, K.; Yamamoto, A. J. Organomet. Chem. 1990, 383, 587. Bardi, R.; Piazzesi, A. M.; Del Pra, A.; Cavinato, G.; Toniolo, L. Inorg. Chim. Acta. 1985, 99, 102.
9. For preliminary communication of part of this work see: Alcock, N. W.; Brown, J. M.; Pérez-Torrente, J. J. Tetrahedron Lett. 1992, 33, 389–393.
10. Fryzuk, M. J.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6262—6269.
11. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932–7934.
12. Kagan, H. B.; Dang, T.-P., J. Am. Chem. Soc. 1972, 94, 6429–6433.
13. Brown, J. M.; Evans, P. L. Tetrahedron 1988, 44, 4905—4918.
14. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158, and references therein.
15. Brown, J. M.; Cooley, N. A. Organometallics 1990, 9, 353–359.
16. Benkeser, R. A.; Hickner, R. A.; Hoke, D. L.; Thomas, U. H. J. Am. Chem. Soc. 1958, 80, 5289.
17. Cozzi, F.; Guenzi, A.; Johnson, C. A.; Mislow, K.; Hounshell, W. D.; Blount, J. F. J. Am. Chem. Soc. 1981, 103, 957–958.
18. Kawano, H.; Ikariya, T.; Ishii, Y.; Kodama, T.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Akutagawa, S. Bull. Chem. Soc. Jpn. 1992, 65, 1595. Mashima, K.; Hino, T.; Takaya, H. J. Chem. Soc., Dalton Trans 1992, 2099. Mashima, K.; Hino, T.; Takaya, H. Tetrahedron Lett. 1991, 32, 3101. Ashby, M. T.; Khan, M. A.; Halpern, J. Organometallics 1991, 10, 2011. Kawano, H.; Ishii, Y.; Kodama, T.; Saburi, M.; Ichida, Y. Chem. Lett. 1987, 1311. Ohta, T.; Takaya, H.; Noyori, R. Inorg. Chem. 1988, 27, 566.
19. Kawano, H.; Ikariya, T.; Ishii, Y.; Kodana, T.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Akutagawa, S. J. Org. Chem. 1994, 59, 3064 and references therein.
20. Alcock, N. W.; Brown, J. M.; Pearson, M.; Woodward, S. Tetrahedron: Asymmetry 1992, 3, 17—20. Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743–756.
21. Using the standard Cahn-Ingold-Prelog conventions for the assignment of atropisomeric chirality and treating the trans P-Pt-C' as one pair of substituents about the Pt-C axis; Prelog, V.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1982, 21, 567—583.
22. Hunter, C. A. Chem. Soc. Rev. 1994, 23, 101–109.
23. Debaerdemaker, T.; Klein, H.-P.; Wiege, M.; Brune, H. A. Z. Naturforsch., B 1981, 36, 958.
24. Brune, H. A.; Wiege, M.; Debaerdemaker, T. Z. Naturforsch., B 1984, 39, 359. Cf: Debaerdemaker, T.; Weisemann, C.; Brune, H. A. Acta Crystallogr., Sect. C. 1987, 43, 1253.
25. Hayashi, T.; Hayashizaki, K.; Kiyoh, T.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 8153–8156.
26. Whitesides, G. M.; Gaasch, J. F.; Stedronsky, E. R. J. Am. Chem. Soc. 1972, 94, 5258.
27. Doyle, M. M.; Jackson, W. R.; Perlmutter, P. Tetrahedron Lett. 1989, 30, 5357.
28. McDermott, J. X.; White, J. F.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6521.
29. Brown, J. M.; Cook, S. J.; Kimber, S. J. J. Organomet. Chem. 1984, 269, C58.
30. Chen, L. S.; Chen, G. J.; Tamborski, C. J. Organomet. Chem. 1981, 215, 281.
31. Sheldrick, G. M. SHELXTL User's Manual; Nicolet Instrument Co.: Madison, WI, 1983, 1986.
32. International Tables for X-Ray Crystallography; Kynoch Press: Birmingham, U.K., 1974; Vol. IV (present distributor Kluwer Academic Publishers, Dordrecht, The Netherlands).