C8K-promoted self-condensation and self-condensation-cycloisomerization reactions of α,β-unsaturated fischer carbene complexes

Angewandte Chemie - International Edition

Volumn 41, Issue 18, 2002, Pages 3442-3445

  Sierra, Miguel A ^a   Ramírez López, Pedro ^a   Gómez Gallego, Mar ^a   Lejon, Tore ^b   Mancheño, María José ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSITY OF TROMSØ   (Norway)

Author keywords

C C coupling; Carbene ligands; Chromium; Dimerization; Radical ions; Tungsten

Indexed keywords

CONDENSATION; GRAPHITE; NEGATIVE IONS; POTASSIUM;

CYCLOISOMERIZATION;

CHEMICAL ANALYSIS;

1 METHYLNAPHTHALENE; CARBENOID; HEMPA;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; ISOMERISM; POLYMERIZATION; REACTION ANALYSIS; REDUCTION;

EID: 0037119655     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20020916)41:18<3442::AID-ANIE3442>3.0.CO;2-Z     Document Type: Article

References (44)

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25. 2. The data were collected with an Enraf-Nonius CAD-4 diffractometer (T=298(2)K). The structure and the refinement of the crystal structure were done with the SHELX97 program. The non-hydrogen atoms were refined anisotropically. CCDC-180496 (9a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac,uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit @ccdc,cam.ac.uk).
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28. a) M. Contento, D. Savoia, C. Trombini, A. Umani-Ronchi, Synthesis 1979, 30; For reductive dimerization of α,β-unsaturated esters see: b) J. Inanaga, Y. Handa, T. Tabuchi, K. Otsubo, M. Yamaguchi, T. Hanamoto, Tetrahedron Lett. 1991, 32, 6557; c) K. Takaki, F. Beppu, S. Tanaka, Y. Tsubaki, T. Jintoku, Y. Fujiwara, J. Chem. Soc. Chem. Commun. 1990. 516; d) I. Fussing, O. Hammerich, A. Hussain, M. Folmer Nielsen, J. H. P. Utley, Acta Chem. Scand. 1998, 52, 328.
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30. 5; 70%.
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32. The dimerization of chromium carbene α anions is known, a) L. Lattuada, E. Licandro, S. Maiorana, H. Molinari, A. Papagni, Organometallics 1991, 10, 807; b) A. Geisbauer, S. Mihan, W. Beck, J. Organomet. Chem. 1995, 501, 61.
33. a) H.-P. Wu, R. Aumann, R. Fröhlich, B. Wibbeling, O. Kataeva, Chem. Eur. J. 2001, 7, 5084; b) K. Ohe, T. Yokoi, K. Miki, F. Nishino, S. Uemura, J. Am. Chem. Soc. 2002, 124, 526; c) T. Miura, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 518; For related cyclizations see: d) J. Barluenga, F. Aznar, S. Barluenga, M. Fernández, A. Martín, S. García-Granda, A. Piñera-Nicolás, Chem. Eur. J 1998, 4, 2280.
34. a) H.-P. Wu, R. Aumann, R. Fröhlich, B. Wibbeling, O. Kataeva, Chem. Eur. J. 2001, 7, 5084; b) K. Ohe, T. Yokoi, K. Miki, F. Nishino, S. Uemura, J. Am. Chem. Soc. 2002, 124, 526; c) T. Miura, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 518; For related cyclizations see: d) J. Barluenga, F. Aznar, S. Barluenga, M. Fernández, A. Martín, S. García-Granda, A. Piñera-Nicolás, Chem. Eur. J 1998, 4, 2280.
35. a) H.-P. Wu, R. Aumann, R. Fröhlich, B. Wibbeling, O. Kataeva, Chem. Eur. J. 2001, 7, 5084; b) K. Ohe, T. Yokoi, K. Miki, F. Nishino, S. Uemura, J. Am. Chem. Soc. 2002, 124, 526; c) T. Miura, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 518; For related cyclizations see: d) J. Barluenga, F. Aznar, S. Barluenga, M. Fernández, A. Martín, S. García-Granda, A. Piñera-Nicolás, Chem. Eur. J 1998, 4, 2280.
36. a) H.-P. Wu, R. Aumann, R. Fröhlich, B. Wibbeling, O. Kataeva, Chem. Eur. J. 2001, 7, 5084; b) K. Ohe, T. Yokoi, K. Miki, F. Nishino, S. Uemura, J. Am. Chem. Soc. 2002, 124, 526; c) T. Miura, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 518; For related cyclizations see: d) J. Barluenga, F. Aznar, S. Barluenga, M. Fernández, A. Martín, S. García-Granda, A. Piñera-Nicolás, Chem. Eur. J 1998, 4, 2280.
37. A reviewer has suggested an alternate mechanism. Monoprotonation of 13 would give intermediate 17 which by cyclization by the addition of the enolate anion of one carbene complex to the other neutral carbene would yield the final product 9.
38. a) M. A, Sierra, M. J. Mancheño, E. Sáez, J. C. del Amo, J. Am. Chem. Soc. 1998, 120, 6812;
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40. Compounds 16 were unstable products and considerable loss of material was observed upon chromatographic purification.
41. R. Aumann, Eur. J. Org. Chem. 2000, 17.
42. Complexes 6 and 7 were prepared by procedures previously described in the literature, a) 6a-d: R. Aumann, H. Heinen, Chem. Ber 1987, 120, 537;
43. b) 7a: R. Aumann, P. Hinterding, Chem. Ber. 1993, 126, 421;
44. c) 7b: I. Fernández, M. A. Sierra, M. J. Mancheño, M, Gómez-Gallego, S. Ricart, Organometallics 2001, 20, 4304.