Organic syntheses via transition metal complexes. 104. Cyclopentadienyl thiolacylates from (1-alkynyl)carbene complexes (M = Cr, W): sulfur-centered fragmentation of ligand side chains

Organometallics

Volumn 19, Issue 12, 2000, Pages 2373-2381

  Wu, He Ping ^a   Aumann, Rudolf ^a   Fröhlich, Roland ^a   Wegelius, Elina ^a   Saavenketo, Pauli ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CARBOXYLIC ACIDS; CHEMICAL BONDS; CHROMIUM; ISOMERS; SULFUR; SYNTHESIS (CHEMICAL); TUNGSTEN;

ALKYNYL CARBENE COMPLEXES; CYCLOPENTADIENES; CYCLOPENTADIENYL THIOLACYLATES;

ORGANOMETALLICS;

EID: 0033714542     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om000107v     Document Type: Article

References (26)

1. Part 103: Aumann, R.; Kössmeier, M.; Roths, K.; Fröhlich, R. Tetrahedron, in press.
2. For a recent review on (1-alkynyl)carbene complexes see: Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 163-242.
3. For a recent review on 1-metalla-1,3,5-hexatrienes and related compounds see: Aumann, R. Eur. J. Org. Chem. 2000, 17-31.
4. For a recent review on the preparation of five-membered carbocyclic rings from Fischer carbene complexes see: Herndon, J. W. Tetrahedron 2000, 56, 1257-1280.
5. For related studies, in which 1-metalla-13,5-trienes were generated by addition of dienes to (1alkynyl)carbene complexes, see: Barluenga, J.; Aznar, F.; Barluenga, S.; Fernández, M.; Martín, A.; García-Granda, S.; Pinera-Nicolás A. Chem. Eur. J. 1998, 4, 2280-2298.
6. Aumann, R.; Fröhlich, R. Organometallics 1999, 8, 369-1380.
7. Wu, H.; Aumann, R.; Fröhlich, R. Eur. J. Org. Chem. 2000, 1183-1192.
8. For reviews see: (a) Voss, J. In Houben-Weyl, Methods of Organic Chemistry; Georg Thieme Verlag: Stuttgart, Germany, 1985; Vol. E11, pp 188-231. (b) Schaumann, E. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, U.K., 1999; Chapter 17. (c) Metzner, P. Synthesis 1992, 1185-1199. (d) Molina, M. T.; Yanez, M.; Mo, O.; Notario, R.; Abboud, J.-L. M. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, U.K., 1997; Supplement A3, Chapter 23.
9. For reviews see: (a) Voss, J. In Houben-Weyl, Methods of Organic Chemistry; Georg Thieme Verlag: Stuttgart, Germany, 1985; Vol. E11, pp 188-231. (b) Schaumann, E. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, U.K., 1999; Chapter 17. (c) Metzner, P. Synthesis 1992, 1185-1199. (d) Molina, M. T.; Yanez, M.; Mo, O.; Notario, R.; Abboud, J.-L. M. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, U.K., 1997; Supplement A3, Chapter 23.
10. For reviews see: (a) Voss, J. In Houben-Weyl, Methods of Organic Chemistry; Georg Thieme Verlag: Stuttgart, Germany, 1985; Vol. E11, pp 188-231. (b) Schaumann, E. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, U.K., 1999; Chapter 17. (c) Metzner, P. Synthesis 1992, 1185-1199. (d) Molina, M. T.; Yanez, M.; Mo, O.; Notario, R.; Abboud, J.-L. M. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, U.K., 1997; Supplement A3, Chapter 23.
11. For reviews see: (a) Voss, J. In Houben-Weyl, Methods of Organic Chemistry; Georg Thieme Verlag: Stuttgart, Germany, 1985; Vol. E11, pp 188-231. (b) Schaumann, E. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, U.K., 1999; Chapter 17. (c) Metzner, P. Synthesis 1992, 1185-1199. (d) Molina, M. T.; Yanez, M.; Mo, O.; Notario, R.; Abboud, J.-L. M. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, U.K., 1997; Supplement A3, Chapter 23.
12. (a) Vallée, Y. Rev. Heteroat. Chem. 1993, 8, 1-20.
13. (b) Pelloux-Léon, N. In Gas-Phase Reactions in Organic Synthesis; Vallée, Y., Ed.; Gordon and Breach: Amsterdam, 1997; Chapter 6.
14. (a) Metzner, B.; Vialle, J. Bull. Soc. Chim. Fr. 1972, 3138-3145.
15. (b) Metzner, B.; Vialle, J. Bull. Soc. Chim. Fr. 1973, 1317-1325.
16. (c) Metzner, B.; Vialle, J. Bull. Soc. Chim. Fr. 1973, 1703-1707.
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18. (a) Pauli, A.; Meier, H. Chem. Ber. 1987, 120, 1617-1620.
19. (b) Aumann, R.; Göttker-Schnetmann, L; Fröhlich, R. Eur. J. Org. Chem. 1999, 2545-2561.
20. Aumann, R.; Jasper, B.; Läge, M.; Krebs, B. Organometallics 1994, 13, 3502-3509.
21. Data sets were collected with Nonius MACH3 and KappaCCD diffractometers, equipped with a Nonius FR591 rotating anode generator. Programs used: data collection EXPRESS (Nonius BV, 1994) and COLLECT (Nonius BV, 1998), data reduction MolEN (K. Fair, Enraf-Nonius BV, 1990) and Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326), absorption correction for CCD data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997). graphics DIAMOND (Brandenburg, K. Universität Bonn, 1997).
22. Data sets were collected with Nonius MACH3 and KappaCCD diffractometers, equipped with a Nonius FR591 rotating anode generator. Programs used: data collection EXPRESS (Nonius BV, 1994) and COLLECT (Nonius BV, 1998), data reduction MolEN (K. Fair, Enraf-Nonius BV, 1990) and Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326), absorption correction for CCD data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997). graphics DIAMOND (Brandenburg, K. Universität Bonn, 1997).
23. Data sets were collected with Nonius MACH3 and KappaCCD diffractometers, equipped with a Nonius FR591 rotating anode generator. Programs used: data collection EXPRESS (Nonius BV, 1994) and COLLECT (Nonius BV, 1998), data reduction MolEN (K. Fair, Enraf-Nonius BV, 1990) and Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326), absorption correction for CCD data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997). graphics DIAMOND (Brandenburg, K. Universität Bonn, 1997).
24. Data sets were collected with Nonius MACH3 and KappaCCD diffractometers, equipped with a Nonius FR591 rotating anode generator. Programs used: data collection EXPRESS (Nonius BV, 1994) and COLLECT (Nonius BV, 1998), data reduction MolEN (K. Fair, Enraf-Nonius BV, 1990) and Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326), absorption correction for CCD data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997). graphics DIAMOND (Brandenburg, K. Universität Bonn, 1997).
25. Data sets were collected with Nonius MACH3 and KappaCCD diffractometers, equipped with a Nonius FR591 rotating anode generator. Programs used: data collection EXPRESS (Nonius BV, 1994) and COLLECT (Nonius BV, 1998), data reduction MolEN (K. Fair, Enraf-Nonius BV, 1990) and Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326), absorption correction for CCD data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997). graphics DIAMOND (Brandenburg, K. Universität Bonn, 1997).
26. Data sets were collected with Nonius MACH3 and KappaCCD diffractometers, equipped with a Nonius FR591 rotating anode generator. Programs used: data collection EXPRESS (Nonius BV, 1994) and COLLECT (Nonius BV, 1998), data reduction MolEN (K. Fair, Enraf-Nonius BV, 1990) and Denzo-SMN (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326), absorption correction for CCD data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37. Blessing, R. H. J. Appl. Crystallogr. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997). graphics DIAMOND (Brandenburg, K. Universität Bonn, 1997).