Reactions of thioketones possessing a conjugated C=C bond with diazo compounds

Helvetica Chimica Acta

Volumn 89, Issue 12, 2006, Pages 3041-3055

  Egli, Daniel H ^a   Linden, Anthony ^a   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZO COMPOUNDS; ELECTROCYCLIZATION; THIIRANES; THIOKETONES;

ADDITION REACTIONS; AMINES; CHEMICAL BONDS; DESULFURIZATION; REACTION KINETICS; SULFUR COMPOUNDS; UNSATURATED COMPOUNDS; X RAY CRYSTALLOGRAPHY;

KETONES;

1 (2,5 DIHYDRO 4,5 DIPHENYLTHIOPHEN 2YL)PIPERIDINE; 1 (2,5 DIHYDRO 4,5,5 TRIPHENYLTHIOPHEN 2 YL)PIPERIDINE; 1 (4 PHENYL 1 THIASPIROL[4.5]DEC 3 EN 2 YL)PIPERIDINE; 2 [[(BUTYL)(1 OXOCYCLOHEX 1 EN 1 YL)METHYL]SULFANYL] 1,3 DIHYDRO 2H ISOINDOLE 1,3 DIONE; 2,5 DIHYDROTHIOPHENE DERIVATIVE; 3 (1 BUTYL 2,2, DIPHENYLETHENYL)CYCLOHEX 2 EN 1 ONE; 3 (1,2,2 TRIPHENYLETHENYL)CYCLOHEX 2 EN 1 ONE; 3,4 DIHYDRO 2,4,6 TRIPHENYL 3 (2,3,3 TRIPHENYLTHIIRAN 2 YL) 2H THIOPYRANE; CARBONYL DERIVATIVE; THIOKETONE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 33846171210     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200690274     Document Type: Article

References (34)

1. J. Buter, S. Wassenaar, R. M. Kellogg, J. Org. Chem. 1972, 37, 4045.
2. G. Mlostoń, R. Huisgen, Heterocycles 1985, 23, 2201.
3. G. Mlostoń, T. Gedenk, H. Heimgartner, Helv. Chim. Acta 1996, 79, 1537.
4. G. Mlostoń, H. Heimgartner, Pol. J. Chem. 2000, 74, 1503.
5. G. Mloston, H. Heimgartner, in 'The Chemistry of Heterocyclic Compounds, Vol. 59, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products', Eds. A. Padwa, W. H. Pearson, John Wiley & Sons, New York, 2002, p. 315.
6. A. Schönberg, D. Cernik, W. Urban, Ber. Dtsch. Chem. Ges. 1931, 64, 2577.
7. R. Huisgen, I. Kalwinsch, X. Li, G. Mlostoń, Eur. J. Org. Chem. 2000, 1685.
8. C. Bak, K. Praefcke, Chem. Ber. 1979, 112, 2744.
9. M. Kägi, A. Linden, G. Mlostoń, H. Heimgartner, Helv. Chim. Acta 1996, 79, 855.
10. M. Kägi, A. Linden, G. Mlostoń, H. Heimgartner, Helv. Chim. Acta 1998, 81, 285.
11. B. Kelmendi, G. Mlostoń, H. Heimgartner, Heterocycles 2000, 52, 475.
12. D. H. Egli, A. Linden, H. Heimgartner, Helv. Chim. Acta 2006, 89, 1910.
13. D. H. Egli, A. Linden, H. Heimgartner, Helv. Chim. Acta, in press.
14. T. Saito, H. Fujii, S. Hayashibe, T. Matsushita, H. Kato, K. Kobayashi, J. Chem. Soc., Perkin Trans. 1 1996, 1897.
15. G. M. Li, S. Niu, M. Segi, K. Tanaka, T. Nakajima, R. A. Zingaro, J. H. Reibenspies, M. B. Hall, J. Org. Chem. 2000, 65, 6601.
16. C. K. Johnson, ORTEPII, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
17. J. E. McMurry, W. A. Andrus, J. H. Musser, Synth. Commun. 1978, 8, 53.
18. A. P. Kozikowski, S. H. Jung, J. Org. Chem. 1986, 51, 3400.
19. G. Capozzi, S. Menichetti, C. Nativi, A. Rosi, G. Valle, Tetrahedron 1992, 48, 9023.
20. F. Clesse, H. Quiniou, Bull Soc. Chim. Fr. 1969, 1940.
21. D. S. Wulfman, S. Yousefian, J. M. White, Synth. Commun. 1988, 18, 2349.
22. F. Arndt, Org. Synth. 1935, 15, 3.
23. T. L. Holton, H. Shechter, J. Org. Chem. 1995, 60, 4725.
24. M. U Bombala, S. V. Ley, J. Chem. Soc., Perkin Trans. 1 1979, 3013.
25. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
26. Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A, Eds. C. W. Carter Jr., R. M. Sweet, Academic Press, New York, 1997, p. 307.
27. R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33.
28. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435.
29. a) E. N. Maslen, A. G. Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 6.1.1.1, p. 477;
30. b) D. C. Creagh, W. J. McAuley, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 4.2.6.8, p. 219;
31. c) D. C. Creagh, J. H. Hubbell, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 4.2.4.3, p. 200.
32. R. F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
33. J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
34. G. M. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures, University of Göttigen, Germany, 1997.