A Restitutive Bergman Rearrangement: Synthesis of a CpCo-Complexed, Tetraethynylated Cyclobutadiene

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 10, 1997, Pages 1107-1109

  Altmann, Markus ^a   Roidl, Gaby ^a   Enkelmann, Volker ^a   Bunz, Uwe H F ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

Alkynes; Carbocyles; Cobalt; Rearrangements

Indexed keywords

EID: 0030873208     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199711071     Document Type: Article

References (54)

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35. b) hexaethynylbenzene: R. Diercks, J. C. Armstrong, R. Boese, K. P. C. Vollhardt, ibid. 1986, 98, 270 and 1986, 26, 268; R. Boese, J. R. Green, J. Mittendorf, D. L. Mohler, K. P. C. Vollhardt, ibid. 1992, 104, 1643 and 1992, 31, 1643;
36. b) hexaethynylbenzene: R. Diercks, J. C. Armstrong, R. Boese, K. P. C. Vollhardt, ibid. 1986, 98, 270 and 1986, 26, 268; R. Boese, J. R. Green, J. Mittendorf, D. L. Mohler, K. P. C. Vollhardt, ibid. 1992, 104, 1643 and 1992, 31, 1643;
37. b) hexaethynylbenzene: R. Diercks, J. C. Armstrong, R. Boese, K. P. C. Vollhardt, ibid. 1986, 98, 270 and 1986, 26, 268; R. Boese, J. R. Green, J. Mittendorf, D. L. Mohler, K. P. C. Vollhardt, ibid. 1992, 104, 1643 and 1992, 31, 1643;
38. b) hexaethynylbenzene: R. Diercks, J. C. Armstrong, R. Boese, K. P. C. Vollhardt, ibid. 1986, 98, 270 and 1986, 26, 268; R. Boese, J. R. Green, J. Mittendorf, D. L. Mohler, K. P. C. Vollhardt, ibid. 1992, 104, 1643 and 1992, 31, 1643;
39. c) tetraethynylethylene: H. Hauptmann, ibid. 1975, 87, 490 and 1975, 14, 498; H. Hauptmann, Tetrahedron Lett. 1975, 1931; K. P. C. Vollhardt, L. S. Winn, ibid. 1985, 709; H. Hopf, M. Kreutzer, P. G. Jones, Chem. Ber. 1991, 124, 1471; R. Faust, F. Diederich, V. Gramlich, P. Seiler, Chem. Eur. J. 1995, 1, 111; Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. Engl. 1991, 30, 698; J. Anthony, C. B. Knobler, F. Diederich, ibid. 1993, 105, 437 and 1993, 32, 406; R. R. Tykwinski, F. Diederich, Liebigs Ann. 1997, 649, and references therein;
40. c) tetraethynylethylene: H. Hauptmann, ibid. 1975, 87, 490 and 1975, 14, 498; H. Hauptmann, Tetrahedron Lett. 1975, 1931; K. P. C. Vollhardt, L. S. Winn, ibid. 1985, 709; H. Hopf, M. Kreutzer, P. G. Jones, Chem. Ber. 1991, 124, 1471; R. Faust, F. Diederich, V. Gramlich, P. Seiler, Chem. Eur. J. 1995, 1, 111; Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. Engl. 1991, 30, 698; J. Anthony, C. B. Knobler, F. Diederich, ibid. 1993, 105, 437 and 1993, 32, 406; R. R. Tykwinski, F. Diederich, Liebigs Ann. 1997, 649, and references therein;
41. c) tetraethynylethylene: H. Hauptmann, ibid. 1975, 87, 490 and 1975, 14, 498; H. Hauptmann, Tetrahedron Lett. 1975, 1931; K. P. C. Vollhardt, L. S. Winn, ibid. 1985, 709; H. Hopf, M. Kreutzer, P. G. Jones, Chem. Ber. 1991, 124, 1471; R. Faust, F. Diederich, V. Gramlich, P. Seiler, Chem. Eur. J. 1995, 1, 111; Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. Engl. 1991, 30, 698; J. Anthony, C. B. Knobler, F. Diederich, ibid. 1993, 105, 437 and 1993, 32, 406; R. R. Tykwinski, F. Diederich, Liebigs Ann. 1997, 649, and references therein;
42. c) tetraethynylethylene: H. Hauptmann, ibid. 1975, 87, 490 and 1975, 14, 498; H. Hauptmann, Tetrahedron Lett. 1975, 1931; K. P. C. Vollhardt, L. S. Winn, ibid. 1985, 709; H. Hopf, M. Kreutzer, P. G. Jones, Chem. Ber. 1991, 124, 1471; R. Faust, F. Diederich, V. Gramlich, P. Seiler, Chem. Eur. J. 1995, 1, 111; Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. Engl. 1991, 30, 698; J. Anthony, C. B. Knobler, F. Diederich, ibid. 1993, 105, 437 and 1993, 32, 406; R. R. Tykwinski, F. Diederich, Liebigs Ann. 1997, 649, and references therein;
43. c) tetraethynylethylene: H. Hauptmann, ibid. 1975, 87, 490 and 1975, 14, 498; H. Hauptmann, Tetrahedron Lett. 1975, 1931; K. P. C. Vollhardt, L. S. Winn, ibid. 1985, 709; H. Hopf, M. Kreutzer, P. G. Jones, Chem. Ber. 1991, 124, 1471; R. Faust, F. Diederich, V. Gramlich, P. Seiler, Chem. Eur. J. 1995, 1, 111; Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. Engl. 1991, 30, 698; J. Anthony, C. B. Knobler, F. Diederich, ibid. 1993, 105, 437 and 1993, 32, 406; R. R. Tykwinski, F. Diederich, Liebigs Ann. 1997, 649, and references therein;
44. c) tetraethynylethylene: H. Hauptmann, ibid. 1975, 87, 490 and 1975, 14, 498; H. Hauptmann, Tetrahedron Lett. 1975, 1931; K. P. C. Vollhardt, L. S. Winn, ibid. 1985, 709; H. Hopf, M. Kreutzer, P. G. Jones, Chem. Ber. 1991, 124, 1471; R. Faust, F. Diederich, V. Gramlich, P. Seiler, Chem. Eur. J. 1995, 1, 111; Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. Engl. 1991, 30, 698; J. Anthony, C. B. Knobler, F. Diederich, ibid. 1993, 105, 437 and 1993, 32, 406; R. R. Tykwinski, F. Diederich, Liebigs Ann. 1997, 649, and references therein;
45. c) tetraethynylethylene: H. Hauptmann, ibid. 1975, 87, 490 and 1975, 14, 498; H. Hauptmann, Tetrahedron Lett. 1975, 1931; K. P. C. Vollhardt, L. S. Winn, ibid. 1985, 709; H. Hopf, M. Kreutzer, P. G. Jones, Chem. Ber. 1991, 124, 1471; R. Faust, F. Diederich, V. Gramlich, P. Seiler, Chem. Eur. J. 1995, 1, 111; Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. Engl. 1991, 30, 698; J. Anthony, C. B. Knobler, F. Diederich, ibid. 1993, 105, 437 and 1993, 32, 406; R. R. Tykwinski, F. Diederich, Liebigs Ann. 1997, 649, and references therein;
46. c) tetraethynylethylene: H. Hauptmann, ibid. 1975, 87, 490 and 1975, 14, 498; H. Hauptmann, Tetrahedron Lett. 1975, 1931; K. P. C. Vollhardt, L. S. Winn, ibid. 1985, 709; H. Hopf, M. Kreutzer, P. G. Jones, Chem. Ber. 1991, 124, 1471; R. Faust, F. Diederich, V. Gramlich, P. Seiler, Chem. Eur. J. 1995, 1, 111; Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. Engl. 1991, 30, 698; J. Anthony, C. B. Knobler, F. Diederich, ibid. 1993, 105, 437 and 1993, 32, 406; R. R. Tykwinski, F. Diederich, Liebigs Ann. 1997, 649, and references therein;
47. c) tetraethynylethylene: H. Hauptmann, ibid. 1975, 87, 490 and 1975, 14, 498; H. Hauptmann, Tetrahedron Lett. 1975, 1931; K. P. C. Vollhardt, L. S. Winn, ibid. 1985, 709; H. Hopf, M. Kreutzer, P. G. Jones, Chem. Ber. 1991, 124, 1471; R. Faust, F. Diederich, V. Gramlich, P. Seiler, Chem. Eur. J. 1995, 1, 111; Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. Engl. 1991, 30, 698; J. Anthony, C. B. Knobler, F. Diederich, ibid. 1993, 105, 437 and 1993, 32, 406; R. R. Tykwinski, F. Diederich, Liebigs Ann. 1997, 649, and references therein;
48. c) tetraethynylethylene: H. Hauptmann, ibid. 1975, 87, 490 and 1975, 14, 498; H. Hauptmann, Tetrahedron Lett. 1975, 1931; K. P. C. Vollhardt, L. S. Winn, ibid. 1985, 709; H. Hopf, M. Kreutzer, P. G. Jones, Chem. Ber. 1991, 124, 1471; R. Faust, F. Diederich, V. Gramlich, P. Seiler, Chem. Eur. J. 1995, 1, 111; Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. Engl. 1991, 30, 698; J. Anthony, C. B. Knobler, F. Diederich, ibid. 1993, 105, 437 and 1993, 32, 406; R. R. Tykwinski, F. Diederich, Liebigs Ann. 1997, 649, and references therein;
49. c) tetraethynylethylene: H. Hauptmann, ibid. 1975, 87, 490 and 1975, 14, 498; H. Hauptmann, Tetrahedron Lett. 1975, 1931; K. P. C. Vollhardt, L. S. Winn, ibid. 1985, 709; H. Hopf, M. Kreutzer, P. G. Jones, Chem. Ber. 1991, 124, 1471; R. Faust, F. Diederich, V. Gramlich, P. Seiler, Chem. Eur. J. 1995, 1, 111; Y. Rubin, C. B. Knobler, F. Diederich, Angew. Chem. 1991, 103, 708; Angew. Chem. Int. Ed. Engl. 1991, 30, 698; J. Anthony, C. B. Knobler, F. Diederich, ibid. 1993, 105, 437 and 1993, 32, 406; R. R. Tykwinski, F. Diederich, Liebigs Ann. 1997, 649, and references therein;
50. d) N. Jux, K. Holczer, Y. Rubin, ibid. 1996, 108, 2116
51. and 1996, 35, 1986;
52. U. H. F. Bunz, V. Enkelmann, J. Räder, Organometallics 1993, 12, 4745.
53. w = 0.083. Further details of the crystal structure investigation may be obtained from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen (Germany) on quoting the depository number CSD-406909.
54. J. L. Hencher in The Chemistry of the Functional Groups, The Chemistry of the Carbon-Carbon Triple Bond, Part 1 (Ed.: S. Patai), Wiley, Chichester, 1978, p. 57.