Synthesis and structure of allenyl-substituted η6-benzene(tricarbonyl)chromium complexes

Chemische Berichte

Volumn 130, Issue 8, 1997, Pages 1135-1139

  Müller, Thomas J J ^a   Ansorge, Markus ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001372977     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19971300816     Document Type: Article

References (31)

1. For comprehensive reviews of allene chemistry see, e.g. D. R. Taylor, Chem. Rev. 1967, 67, 317-359;
2. T. F. Rutledge, Acetylenes and Allenes, Reinhold Book Corporation, New York, Amsterdam, London, 1969, parts 1-3; W. T. Brady in The Chemistry of Ketenes, Allenes and Related Compounds, part 1, (Ed.: S. Patai), J. Wiley & Sons, Chichester, New York, Brisbane, Toronto, 1980, 298-308; H. Hopf in The Chemistry of Ketenes, Allenes and Related Compounds, part 2, (Ed.: S. Patai), J. Wiley & Sons, Chichester, New York, Brisbane, Toronto, 1980,
3. 779-902; W. Smadja, Chem. Rev. 1983, 83, 263-320;
4. D. J. Pasto, Tetrahedron 1984, 40, 2805-2827;
5. H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, J. Wiley & Sons, Chichester, New York, Brisbane, Toronto, 1984.
6. For excellent reviews on enyne and enallene cytostatics see, e.g. K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453-1481; Angew. Chem. Int. Ed. Engl. 1991, 50, 1387-1415;
7. K. C. Nicolaou, A. L. Smith in Modern Acetylene Chemistry, (Eds. P. J. Stang, F. Diederich), VCH, Weinheim, 1995, 203-283.
8. See, e.g. H.-J. Altenbach, R. Korff, Tetrahedron Lett. 1984, 22, 5175-5178;
9. F. Palacios, D. Aparicio, J. Garcia, Tetrahedron, 1996, 52, 9609-9628.
10. For a very recent example, see J. W. Grissom, D. Klingberg, D. Huang, B. J. Slattery, J. Org. Chem. 1997, 62, 603-626, and references cited therein.
11. K. Schlögl, A. Mohar, Monatsh. Chem. 1962, 93, 861-876;
12. K. Schlögl, M. Widhalm, Monatsh. Chem. 1981, 112, 91-104;
13. M. Buchmeister, H. Schottenberger, Organometallics 1993, 12, 2472-2477;
14. B. Bildstein, H. Kopacka, M. Schweiger, E. Ellmerer-Müller, K. H. Ongania, K. Wurst, Organometallics 1996, 75, 4398-4406.
15. K. Nunn, P. Messet, R. Greé, R. W. Saalfrank, K. Peters, H. G. von Schnering, Angew. Chem. 1992, 104, 228-229; Angew. Chem. Int. Ed. Engl 1992, 31, 224-225.
16. T. J. J. Müller, H. J. Lindner, Chem. Ber. 1996, 729, 607-613;
17. T. J. J. Müller, M. Ansorge, H. J. Lindner, Chem. Ber. 1996, 129, 1433-1440;
18. T. J. J. Müller, Tetrahedron Lett. 1997, 38, 1025-1028.
19. for excellent reviews for nucleophilic additions see, e.g. M. F. Semmelhack in Comprehensive Organometallic Chemistry II, E. W. Abel, F. G. A. Stone, G. Wilkinson, Eds., Pergamon 1995, Vol. 12, pp. 979-1015; for ring lithiations see, e.g. M. F. Semmelhack, ibid., Vol. 12, pp. 1017-1038; for side chain activation see, e.g. S. G. Davies, T. D. McCarthy, ibid., Vol. 12, pp. 1039-1070; for stabilization of positive charge in the benzylic positions see, e.g. S. G. Davies, T. J. Donohoe, Synlett 1993, 323-332.
20. For a recent example see, e.g. R. W. Saalfrank, A. Welch, M. Haubner, U. Bauer, Liebigs Ann. 1996, 171-181.
21. 3 complexes see, e.g. [10a] J. F. Carpentier, F. Petit, A. Mortreux, V. Dufaud, J.-M. Basset, J. Thivolle-Cazat, J. Mol. Catal. 1993, 81, 1-15.
22. [10b] M. Uemura, H. Nishimura, T. Hayashi, Tetrahedron Lett. 1993, 34, 107-110.
23. [10c] M. Uemura, H. Nishimura, K. Kamikawa, Y. Hayashi, Tetrahedron Lett. 1994, 35, 1909-1912.
24. For palladium catalyzed couplines of alkyne derivatives with manganese and iron K-complexes see, e.g.
25. [10d] U. H. F. Bunz, Pure Appl. Chem. 1996, 68, 309-312 and references cited therein.
26. Surprisingly, the propargylic alcohols 3a, c do not furnish the expected chloro allenes but the corresponding propargylic chloride derivatives. Basically, the fragmentation of the initially formed chloro sulfenyl ester gives rise to two possible products: the propargylic chloride and the "rearranged" allenyl chloride. Obviously, the stability of the propargylic carbenium ion has a crucial influence on the product distribution chloro allene/allenyl chloride, i.e. the higher the stabilization of the carbenium ion the more chloro allene is formed. Besides, another competing reaction is the β-elimination to give the enyne product (together with 4a).
27. T. Jeffery-Luong, G. Linstrumelle, Synthesis 1983, 32-34.
28. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: int. code +44(0)1223/336-033, e-mail: deposit@chemcrys.cam.ac.uk).
29. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. 2 1987, S1-S19.
30. Various editors, Organikum, 13th edition, VEB Deutscher Verlag der Wissenschaften, Berlin, 1974.
31. C. A. L. Mahaffy, P. L. Pauson, Inorg. Synth. 1979, 19, 154-158.