Metal mediated cyclooligomerization of mono- and diazulenylethynes

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2859-2862

  Elwahy, Ahmed H M ^a   Hafner, Klaus ^a  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Azulenylbenzenes; Azulenylcyclobutadienes; Cobalt catalyst; Ethynylazulenes

Indexed keywords

ACETYLENE DERIVATIVE; DIAZULENYLETHYNE; MONOAZULENYLETHYNE; UNCLASSIFIED DRUG;

ANISOTROPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; COMPLEX FORMATION; CRYSTALLIZATION; DERIVATIZATION; DRUG SYNTHESIS; OLIGOMERIZATION;

EID: 0034655460     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00309-9     Document Type: Article

References (23)

1. Fabian, K. H. H.; Elwahy, A. H. M.; Hafner, K. Tetrahedron Lett. 2000, 41, 2855-2858.
2. Elwahy, A. H. M.; Fabian, K. H. H.; Hafner, K., to be published.
3. (a) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Hegedus, L. S., Vol. Ed.; Pergamon: Oxford, 1995; Vol. 12, pp. 741-770.
4. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
5. (c) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596.
6. (d) Stara, I. G.; Stary, I.; Kollarovic, A.; Teply, F.; Vyskocil, S.; Saman, D. Tetrahedron Lett. 1999, 40, 1993-1996.
7. (e) Sato, Y.; Ohashi, K.; Mori, M. Tetrahedron Lett. 1999, 40, 5231-5234.
8. (a) Vollhardt, K. P. C. Acc. Chem. Res. 1977, 10, 1-8.
9. (b) Wakatsuki, Y.; Nomura, O.; Kitaura, K.; Morokuma, K.; Yamazaki, H. J. Am. Chem. Soc. 1983, 105, 1907-1912.
10. (c) Vollhardt, K. P. C. Angew. Chem. 1984, 96, 525-541;
11. Angew. Chem., Int. Ed. Engl. 1984, 23, 539-555.
12. (d) Diercks, R.; Eaton, B. E.; Gürtzgen, S.; Jalisatgi, S.; Matzger, A. J.; Radde, R. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1998, 120, 8247-8248.
13. (e) Hardesty, J. H.; Koerner, J. B.; Albright, T. A.; Lee, G. Y. J. Am. Chem. Soc. 1999, 121, 6055-6067.
14. Ville, G. A.; Vollhardt, K. P. C.; Winter, M. J. Organometallics 1984, 3, 1177-1187. For further mechanistic studies see Ref. 4e.
15. Repeated attempts to cyclotrimerize 2a, b in presence of bis(benzonitrile)palladium chloride or cobaltoctacarbonyl following literature procedures were also unsuccessful. In all cases the starting materials were recovered almost completely. Duchene, K. H.; Vögtle, F. Synthesis 1986, 659-661; Stabel, A.; Herwig, P.; Müllen, K.; Rabe, J. P. Angew. Chem. 1995, 107, 1768-1770; Angew. Chem., Int. Ed. Engl. 1995, 34, 1609-1611; Keegstra, M. A.; De Feyter, S.; De Schryver, F. C.; Müllen, K. Angew. Chem. 1996, 108, 830-833; Angew. Chem., Int. Ed. Engl. 1996, 35, 774-776.
16. Repeated attempts to cyclotrimerize 2a, b in presence of bis(benzonitrile)palladium chloride or cobaltoctacarbonyl following literature procedures were also unsuccessful. In all cases the starting materials were recovered almost completely. Duchene, K. H.; Vögtle, F. Synthesis 1986, 659-661; Stabel, A.; Herwig, P.; Müllen, K.; Rabe, J. P. Angew. Chem. 1995, 107, 1768-1770; Angew. Chem., Int. Ed. Engl. 1995, 34, 1609-1611; Keegstra, M. A.; De Feyter, S.; De Schryver, F. C.; Müllen, K. Angew. Chem. 1996, 108, 830-833; Angew. Chem., Int. Ed. Engl. 1996, 35, 774-776.
17. Repeated attempts to cyclotrimerize 2a, b in presence of bis(benzonitrile)palladium chloride or cobaltoctacarbonyl following literature procedures were also unsuccessful. In all cases the starting materials were recovered almost completely. Duchene, K. H.; Vögtle, F. Synthesis 1986, 659-661; Stabel, A.; Herwig, P.; Müllen, K.; Rabe, J. P. Angew. Chem. 1995, 107, 1768-1770; Angew. Chem., Int. Ed. Engl. 1995, 34, 1609-1611; Keegstra, M. A.; De Feyter, S.; De Schryver, F. C.; Müllen, K. Angew. Chem. 1996, 108, 830-833; Angew. Chem., Int. Ed. Engl. 1996, 35, 774-776.
18. Repeated attempts to cyclotrimerize 2a, b in presence of bis(benzonitrile)palladium chloride or cobaltoctacarbonyl following literature procedures were also unsuccessful. In all cases the starting materials were recovered almost completely. Duchene, K. H.; Vögtle, F. Synthesis 1986, 659-661; Stabel, A.; Herwig, P.; Müllen, K.; Rabe, J. P. Angew. Chem. 1995, 107, 1768-1770; Angew. Chem., Int. Ed. Engl. 1995, 34, 1609-1611; Keegstra, M. A.; De Feyter, S.; De Schryver, F. C.; Müllen, K. Angew. Chem. 1996, 108, 830-833; Angew. Chem., Int. Ed. Engl. 1996, 35, 774-776.
19. Repeated attempts to cyclotrimerize 2a, b in presence of bis(benzonitrile)palladium chloride or cobaltoctacarbonyl following literature procedures were also unsuccessful. In all cases the starting materials were recovered almost completely. Duchene, K. H.; Vögtle, F. Synthesis 1986, 659-661; Stabel, A.; Herwig, P.; Müllen, K.; Rabe, J. P. Angew. Chem. 1995, 107, 1768-1770; Angew. Chem., Int. Ed. Engl. 1995, 34, 1609-1611; Keegstra, M. A.; De Feyter, S.; De Schryver, F. C.; Müllen, K. Angew. Chem. 1996, 108, 830-833; Angew. Chem., Int. Ed. Engl. 1996, 35, 774-776.
20. (a) Sternberg, E. D.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 1564-1573.
21. (b) Macomber, D. W.; Verma, A. G.; Rogers, R. D. Organometallics 1988, 7, 1241-1253.
22. All described new compounds gave correct elemental analyses.
23. 3 with tetramethylsilane as internal standard. UV-vis spectra were recorded with a Beckman UV-5240 spectrometer. Mass spectra (MS) were obtained with a Varian 311A instrument.