Carbocyclic ring expansions with alkyne and carbene sources mediated by nickel(0) complexes: Structure of the critical organonickel intermediates

Tetrahedron

Volumn 54, Issue 7, 1998, Pages 1169-1184

  Eisch, John J ^a   Aradi, Allen A ^a   Lucarelli, Michael A ^a   Qian, Yun ^a  

^a BINGHAMTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; NICKEL COMPLEX; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; OLIGOMERIZATION; PRIORITY JOURNAL;

EID: 0032510202     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10216-2     Document Type: Article

References (24)

1. 1. Part 15 of the series, Organic Chemistry of Subvalent Transition Metal Complexes. Previous part: Eisch, J.J.; Qian, Y.; Singh, M. J. Organomet. Chem. 1996, 512, 207.
2. 2. Reppe, W.; Schlichtling, O.; Klager, K.; Toepel, T. Liebigs Ann. Chem. 1948, 560, 1.
3. 3. Roelen, O. Angew Chem., 1948, A60, 62.
4. 4. Heimbach, P.; Jolly, P.W.; Wilke, G. Advan. Organometal. Chem., 1970, 8, 29.
5. 5. Heimbach, P. Angew. Chem., 1973, 85, 1035.
6. 6. Jolly, P. W.; Wilke, G. The Organic Chemistry of Nickel, Vol. 2, Academic Press, New York, 1975, pp. 133-212.
7. 7. For a review of intermediates and reaction mechanisms in the interaction of nickel(0) complexes with organic substrates: Eisch, J.J.; Sexsmith, S.R. Res. Chem. Intermed. 1990, 13, 149.
8. 8. The use of trimethylsilyl(iso)cyanide as a surrogate for CO in carbonylation reactions was first demonstrated by our group in 1983 (Eisch, J.J.; Aradi, A.A.; Han, K.I. Tetrahedron Lett. 1983, 2073), although many other groups have subsequently employed this reagent without noting our prior work.
9. 9. Eisch, J.J.; Qian, Y.; Singh, M. J. Organomet. Chem. 1996, 512, 207.
10. 10. Private communication from Professor Günther Wilke to J.J. Eisch, 1985.
11. 11. The structure analysis of 20 by XRD has been carried out by Professor Carl Krüger's group at the Max-Planck-Institut für Kohlenforschung, Mülheim (Ruhr), Germany. Details of the structure of 20 along with its chemical reactions will be published jointly by Professor Krüger and us in the near future.
12. 12. Barnett, B.L.; Krüger, C. J. Organomet. Chem. 1972, 42, 169.
13. 13. Vilkov, L.V.; Mastryukov, V.S.; Sadova, N.I. Determination of the Geometrical Structure of Free Molecules, Mir, Moscow, 1983, p. 122.
14. 14. Eisch, J.J.; Damasevitz, G.A. J. Organomet. Chem. 1975, 96, C23.
15. 15. Details are given in this article's Experimental Section.
16. 3SiCN to undergo largely a syn-hydrocyanation (Cf. this Experimental Section).
17. 17. Eisch, J.J.; Piotrowski, A.M.; Aradi, A.A.; Krüger, C.; Romão, M.J. Z. Naturforsch. 1985, 40b, 624.
18. 18. Eisch, J.J.; Galle, J.E.; Aradi, A.A.; Boleslawski, M.P. J. Organometal. Chem. 1986, 312, 399.
19. 17 Contrary to the suggestion of Hoberg and Richter (J. Organomet. Chem. 1980, 195, 355) there is no evidence that such cyclobutadiene-nickel(0) complexes ever are formed from oligomerizing alkynes or from nickeloles.
20. 20. Eisch, J.J.; Behrooz, M.; Dua, S.K. J. Organomet. Chem. 1985, 285, 121.
21. 21. Eisch, J.J.; Piotrowski, A.M.; Han, K.I.; Krüger, C.; Tsay,Y.H. Organometallics 1985, 4, 224.
22. 22. Eisch, J.J.; Galle, J.E. J. Organomet. Chem., 1975, 96, C23.
23. 23. Eisch, J.J. Organometallic Syntheses, Vol. 2, Academic Press, New York, 1981, pp. 3-84.
24. 1H NMR and IR spectra, so elemental analyses were not considered necessary.