Synthesis of 3,7-disubstituted 9-thiatricyclo[3.3.1.03,7]nonane-1,5-dithiol derivatives and crystal structure of tetramethyl 3(4aH)-oxo-1,4-dihydrophenanthro[9,10-a]pentalene-1,2,4,4a-tetracarboxylate

European Journal of Organic Chemistry

Volumn , Issue 11, 1998, Pages 2647-2650

  Dölling, Wolfgang ^a   Vogt, Almut ^a   Baumeister, Ute ^a   Hartung, Helmut ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

9 Thiatricyclo 3.3.1.03,7 nonane; Anchimeric effect; cis Bicyclo 3.3.0 octane 3,7 diones; Lawesson's reagent; Thiolation of cyclic ketones

Indexed keywords

EID: 2842532837     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199811)1998:11<2647::aid-ejoc2647>3.0.co;2-v     Document Type: Article

References (23)

1. S.-O. Lawesson et al., Org. Synth. Coll. Vol. 1990, 7, 372-375.
2. H. Z. Lecher, R. A. Greenwood, K. C. Whitehouse, T. H. Chao, J. Am. Chem. Soc. 1956, 78, 5018-5022.
3. T. Nishio, J. Chem. Soc.,Chem. Commun. 1989, 205-206.
4. M. P. Cava, M. I. Levinson, Tetrahedron 1985, 41, 5061-5087.
5. E. Schaumann, Novel Routes to Thiocarbonyl Compounds, Elsevier, Amsterdam, 1987, vol. 28, p. 251.
6. W. McGregor, D. C. Sherrington, Chem Soc Rev. 1993, 199-204.
7. S. H. Bertz, J. M. Cook, A. Gawish, U. Weiss, Org. Synth. 1986. 64, 27-38.
8. P. Camps, M. A. Estiarte, S. Vázquez, F. Pérez, Synth. Commun. 1995, 25, 1278-1293.
9. H. M. R. Hoffmann, A. M. El-Khawaga, H. H. Oehlerking, Chem. Ber. 1991, 124, 2147.
10. P. Camps, F. J. Luque, M. Orozco, F. Pérez, S. Vázquez, Tetrahedron Lett. 1996, 37, 8605-8608.
11. A. G. Anastassiou, B. Y.-H. Chao, J. Chem. Soc., Chem. Commun. 1972, 277.
12. W. Dölling, H.-M. Siebel, M. Biedermann, H. Hartung, Phosphorus Sulfur Silicon 1996, 113, 263-274.
13. S. Scheibye, B S. Pedersen, S.-O. Lawesson, Bull. Soc. Chim. Belg. 1978, 87, 229-236.
14. S. Scheibye, R. Shabana, S.-O. Lawesson, C. Roemming, Tetrahedron 1982, 38, 993-1001.
15. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc., Perkin Trans. 2 1987, S1-S19.
16. R. V. Williams, V. R. Gadgil, A. Vij, J. M. Cook, G. Kubiak, Q. Huang, J. Chem. Soc., Perkin Trans 1 1997, 1425-1428.
17. M. Dohle, J. Manz, G. K. Paramonov, H. Quast, Chem. Phys. 1995, 197, 91-99.
18. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100863. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2, 1EZ, UK [Fax: int. code + 44(1223)336-033, E-mail: deposit@ccdc.cam.ac.uk].
19. STADI4, Diffractometer Control Program for Windows, Stoe and Cie GmbH, Darmstadt, Germany, 1996.
20. X-RED, Data Reduction Program, Stoe and Cie GmbH, Darmstadt, Germany, 1996.
21. G. M. Sheldrick, Acta Crystallogr. 1990, A46, 467-473.
22. G. M. Sheldrick, SHELXL-93, Program for the Refinement of Crystal Structures, Universität Göttingen, 1993.
23. XPIPC, Molecular Graphics Program Package for Display and Analysis of Stereochemical Data, Version 4.2 for MS-DOS, Siemens Analytical X-Ray Instruments, Inc., Madison, Wisconsin, USA, 1990.