The palladium mediated conversion of 1,6-diazacyclodeca-3,8-diynes to 3,3'-bispyrroles. An unexpected reorganization of an alkyne π-system

Tetrahedron

Volumn 52, Issue 31, 1996, Pages 10383-10388

  Gleiter, Rolf ^a   Ritter, Joachim ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030605923     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00551-0     Document Type: Article

References (21)

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2. 1 Chiusoli, G. P.; Pallini, L.; Terenghi, M. G. Transition Met. Chem. 1985, 10, 350-353; Chiusoli, G. P.; Costa, M.; Pergreffi, P.; Reverberi, S.; Salerno, G. Gazz Chim. Ital. 1985, 11, 691-696; Chiusoli, G. P.; Costa, M.; Maserati, E.; Salerno, G. J. Organomet. Chem. 1983, 255, C35-C38; Chiusoli, G. P.; Costa. M.; Reverberi, S.; Salerno, G.; Terenghi, M. G. Gazz. Chim. Ital. 1987, 117, 695-700.
3. 1 Chiusoli, G. P.; Pallini, L.; Terenghi, M. G. Transition Met. Chem. 1985, 10, 350-353; Chiusoli, G. P.; Costa, M.; Pergreffi, P.; Reverberi, S.; Salerno, G. Gazz Chim. Ital. 1985, 11, 691-696; Chiusoli, G. P.; Costa, M.; Maserati, E.; Salerno, G. J. Organomet. Chem. 1983, 255, C35-C38; Chiusoli, G. P.; Costa. M.; Reverberi, S.; Salerno, G.; Terenghi, M. G. Gazz. Chim. Ital. 1987, 117, 695-700.
4. 1 Chiusoli, G. P.; Pallini, L.; Terenghi, M. G. Transition Met. Chem. 1985, 10, 350-353; Chiusoli, G. P.; Costa, M.; Pergreffi, P.; Reverberi, S.; Salerno, G. Gazz Chim. Ital. 1985, 11, 691-696; Chiusoli, G. P.; Costa, M.; Maserati, E.; Salerno, G. J. Organomet. Chem. 1983, 255, C35-C38; Chiusoli, G. P.; Costa. M.; Reverberi, S.; Salerno, G.; Terenghi, M. G. Gazz. Chim. Ital. 1987, 117, 695-700.
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9. 5 Review: Gleiter, R.; Merger, R. in Modern Acetylene Chemistry, P. J. Stang, F. Diederich (Eds.), VCH, Weinheim, 1995, 285-319; Gleiter, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 27-44.
10. 5 Review: Gleiter, R.; Merger, R. in Modern Acetylene Chemistry, P. J. Stang, F. Diederich (Eds.), VCH, Weinheim, 1995, 285-319; Gleiter, R. Angew. Chem. Int. Ed. Engl. 1992, 31, 27-44.
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12. 7 An X-ray crystallographic study of 2b provides additional evidence for the 3,3-bispyrrole structure; Ritter, J.; Irngartinger, H.; Gleiter, R. unpublished data.
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14. 8 Negishi, E.; Harring, L. S.; Owczarczyk, Z.; Mahamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256; Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1992, 114, 791-792.
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16. 9 Farnier, M.; Soth, S.; Fournari, P. Can. J. Chem. 1976, 54, 1083-1086; Bray, B. L.; Mathies, P. H.; Naef, R.; Solas, D. R.; Tidwell, T.T.; Artis, D. R.; Muchowski, J. M. J. Org. Chem. 1990, 55, 6317-6328.
17. 10 Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag, Berlin, Heidelberg 1980; Heck, R. Palladium Reagents in Organic Synthesis, Academic Press, London 1985; Trost, B. M.; Lee, D. C. J. Am. Chem. Soc. 1988, 110, 7255-7258.
18. 10 Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag, Berlin, Heidelberg 1980; Heck, R. Palladium Reagents in Organic Synthesis, Academic Press, London 1985; Trost, B. M.; Lee, D. C. J. Am. Chem. Soc. 1988, 110, 7255-7258.
19. 10 Tsuji, J. Organic Synthesis with Palladium Compounds, Springer-Verlag, Berlin, Heidelberg 1980; Heck, R. Palladium Reagents in Organic Synthesis, Academic Press, London 1985; Trost, B. M.; Lee, D. C. J. Am. Chem. Soc. 1988, 110, 7255-7258.
20. 11 Gleiter, R.; Kratz, D. Angew. Chem. Int. Ed. Engl. 1990, 29, 276-279.
21. 12 Gleiter, R.; Ritter, J. to be published.