Palladium-catalyzed phosphaketene decarbonylation: Diphosphaureylene intermediates in diphosphene formation

Organometallics

Volumn 16, Issue 22, 1997, Pages 4768-4770

  David, Marie Anne ^a   Wicht, Denyce K ^a   Glueck, David S ^a   Yap, Glenn P A ^b   Liable Sands, Louise M ^b   Rheingold, Arnold L ^b  

^a Dartmouth College   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001417877     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970761j     Document Type: Article

References (27)

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7. 31P NMR spectrum of the mixture after 2 h showed that 2 was formed quantitatively (11 turnovers). The solvent was removed, and the residue was extracted with 5 mL of petroleum ether. Cooling the resulting orange solution to -25 °C gave 21 mg of 2 (70%).
8. (a) Kudo, K.; Hidai, M.; Uchida, Y. J. Organomet. Chem. 1971, 33, 393-398.
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10. 4 was complete, if more 1 was added to the reaction mixture, it was also converted to 2 at a similar rate.
11. 4Pd: C, 69.69; H, 7.63. Found: C, 69.31; H, 7.64.
12. 2) = 34.70%.
13. Kemmitt, R. D. W.; Moore, M. R. Transition Met. Chem. 1993, 18, 348-352. Since the Pd-C distance in 6 (3.068(10) and 3.100(10) Å) is nonbonding (and similar to that in 9 (3.055(6) Å)), the contribution from such an allyl structure is likely to be minor.
14. For related reactions, see: (a) Becher, H. J.; Langer, E. Angew. Chem., Int. Ed. Engl. 1973, 12, 842-843. (b) Appel, R.; Paulen, W. Chem. Ber. 1983, 116, 2371-2373. (c) Appel, R.; Paulen, W. Chem. Ber. 1983, 116, 109-113. (d) King, R. B.; Wu, F.-J.; Holt, E. M. J. Organomet. Chem. 1990, 383, 295-305.
15. For related reactions, see: (a) Becher, H. J.; Langer, E. Angew. Chem., Int. Ed. Engl. 1973, 12, 842-843. (b) Appel, R.; Paulen, W. Chem. Ber. 1983, 116, 2371-2373. (c) Appel, R.; Paulen, W. Chem. Ber. 1983, 116, 109-113. (d) King, R. B.; Wu, F.-J.; Holt, E. M. J. Organomet. Chem. 1990, 383, 295-305.
16. For related reactions, see: (a) Becher, H. J.; Langer, E. Angew. Chem., Int. Ed. Engl. 1973, 12, 842-843. (b) Appel, R.; Paulen, W. Chem. Ber. 1983, 116, 2371-2373. (c) Appel, R.; Paulen, W. Chem. Ber. 1983, 116, 109-113. (d) King, R. B.; Wu, F.-J.; Holt, E. M. J. Organomet. Chem. 1990, 383, 295-305.
17. For related reactions, see: (a) Becher, H. J.; Langer, E. Angew. Chem., Int. Ed. Engl. 1973, 12, 842-843. (b) Appel, R.; Paulen, W. Chem. Ber. 1983, 116, 2371-2373. (c) Appel, R.; Paulen, W. Chem. Ber. 1983, 116, 109-113. (d) King, R. B.; Wu, F.-J.; Holt, E. M. J. Organomet. Chem. 1990, 383, 295-305.
18. 2 has been proposed. Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748-753.
19. (a) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.
20. (b) Brown, J. M.; Guiry, P. J. Inorg. Chim. Acta 1994, 220, 249-259.
21. + 1241.4092, found 1241.4075.
22. Sillett, G.; Ricard, L.; Patois, C.; Mathey, F. J. Am. Chem. Soc. 1992, 114, 9453-9457. It is also possible that the spectrum is a special case of the AÁXX́ system where some of the couplings are equivalent (see Schlaf, M.; Lough, A. J.; Morris, R. H. Organometallics 1997, 16, 1253-1259) or that P-P bond formation has occurred and 12 is a pseudotetrahedral Pd(0) complex of a three-membered ring ligand.
23. Sillett, G.; Ricard, L.; Patois, C.; Mathey, F. J. Am. Chem. Soc. 1992, 114, 9453-9457. It is also possible that the spectrum is a special case of the AÁXX́ system where some of the couplings are equivalent (see Schlaf, M.; Lough, A. J.; Morris, R. H. Organometallics 1997, 16, 1253-1259) or that P-P bond formation has occurred and 12 is a pseudotetrahedral Pd(0) complex of a three-membered ring ligand.
24. For related studies, see: Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039-5040.
25. (a) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933-4941.
26. (b) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857-1867.
27. (c) Low, J. J.; Goddard, W. A., III J. Am. Chem. Soc. 1986, 108, 6115-6128.