Structural insight into (2-Oxy-π-allyl)palladium and -platinum complexes as precursors of oxodimethylenemethane complexes

Organometallics

Volumn 16, Issue 13, 1997, Pages 3038-3043

  Ohsuka, Akihiro ^a   Wardhana, Tjandra W ^a   Kurosawa, Hideo ^a   Ikeda, Isao ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001563643     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om961108j     Document Type: Article

References (26)

1. Ohsuka, A.; Fujimori, T.; Hirao, T.; Kurosawa, H.; Ikeda, I. J. Chem. Soc., Chem. Commun. 1993, 1039.
2. Ohsuka, A.; Hirao, T.; Kurosawa, H.; Ikeda, I. Organometallics 1995, 14, 2538.
3. Gu, X.-P.; Nishida, N.; Ikeda, I.; Okahara, M. J. Org. Chem. 1987, 52, 3192.
4. Ikeda, I.; Ohsuka, A.; Tani, K.; Hirao, T.; Kurosawa, H. J. Org. Chem. 1996, 61, 4971-4974.
5. 3-Allylpalladium and -platinum complexes (θ + ′ = 61-72°): (a) Mason, R.; Wheeler, A. G. J. Chem. Soc. A 1968, 2549. (b) Hartley, F. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 6, p 721.
6. 3-Allylpalladium and -platinum complexes (θ + ′ = 61-72°): (a) Mason, R.; Wheeler, A. G. J. Chem. Soc. A 1968, 2549. (b) Hartley, F. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 6, p 721.
7. Chen, J.-T.; Huang, T.-M.; Cheng, M.-C.; Lin, Y.-C.; Wang, Y. Organometallics 1992, 11, 1761.
8. For palladium complexes, see: (a) De Munno, G.; Bruno, G.; Rotondo, E.; Giordano, G.; Lo Schiavo, S.; Piraino, P.; Tresoldi, G. Inorg. Chim. Acta 1993, 208, 67. (b) Canty, A. J.; Jin, H.; Roberts, A. S.; Traill, P. R.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1995, 489, 153.
9. For palladium complexes, see: (a) De Munno, G.; Bruno, G.; Rotondo, E.; Giordano, G.; Lo Schiavo, S.; Piraino, P.; Tresoldi, G. Inorg. Chim. Acta 1993, 208, 67. (b) Canty, A. J.; Jin, H.; Roberts, A. S.; Traill, P. R.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1995, 489, 153.
10. Ozawa, F.; Son, T.-i.; Ebina, S.; Osakada, K.; Yamamoto, A. Organometallics 1992, 11, 171.
11. 2, δ 2.19 (s, J(PtH) = 48 Hz).
12. 2, 25 °C, 400 MHz) signals are δ 0.92 (t, 3H), 1.38 (sext, 2H), 1.60 (quint, 2H), 3.65 (t, 2H), 3.39 (d, 1H), 4.13 (d, 1H), 6.45 (dd, 1H).
13. Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y. Tetrahedron Lett. 1982, 23, 4809.
14. Ikeda, I.; Gu, X.-P.; Okuhara, T.; Okahara, M. Synthesis 1990, 32.
15. 18O (purchased as 96.9 atom %-enriched reagent from Isotec Inc., Dayton, OH) and t-BuOK (purified by sublimation before use) in absolute 2-propanol and followed by neutralization with hydrochloric acid.
16. 3-allylpalladium complex: Ohe, K.; Matsuda, H.; Morimoto, T.; Ogoshi, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 1994, 116, 4125.
17. 3-allylpalladium complex: Hoffmann, H. M. R.; Otte, A. R.; Wilde, A.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1.
18. 3-allylpalladium complex: (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (b) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 234. (c) Wilde, A.; Otte, A. R.; Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun. 1993, 615. (d) Otte, A. R.; Wilde, A.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1280.
19. 3-allylpalladium complex: (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (b) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 234. (c) Wilde, A.; Otte, A. R.; Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun. 1993, 615. (d) Otte, A. R.; Wilde, A.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1280.
20. 3-allylpalladium complex: (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (b) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 234. (c) Wilde, A.; Otte, A. R.; Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun. 1993, 615. (d) Otte, A. R.; Wilde, A.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1280.
21. 3-allylpalladium complex: (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173. (b) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 234. (c) Wilde, A.; Otte, A. R.; Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun. 1993, 615. (d) Otte, A. R.; Wilde, A.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1280.
22. (a) Baize, M. W.; Furilla, J. L.; Wojcicki, A. Inorg. Chim. Acta 1994, 223, 1.
23. (b) Huang, T.-M.; Hsu, R.-H.; Yang, C.-S.; Chen, J.-T.; Lee, G.-H.; Wang, Y. Organometallics 1994, 13, 3657.
24. (c) Tsai, F.-Y.; Hsu, R.-H.; Huang, T.-M.; Chen, J.-T.; Lee, G.-H.; Wang, Y. J. Organomet. Chem. 1996, 520, 85.
25. SAPI91: Fan, H.-F. Structure Analysis Programs with Intelligent Control; Rigaku Corp.: Tokyo, Japan, 1991.
26. DIRDIF92: Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; Garcia-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. The DIRDIF program system. Technical Report of the Crystallography Laboratory; University of Nijmegen: Nijmegen, The Netherlands, 1992.