A new approach to 4-alkylthio-1,3-dithiole-2-thione: An unusual reaction of a zinc complex of 1,3-dithole-2-thione-4,5-dithiolate

Organic Letters

Volumn 3, Issue 12, 2001, Pages 1941-1943

  Jia, Chunyang ^a   Zhang, Deqing ^a   Xu, Wei ^a   Zhu, Daoben ^a  

^a INSTITUTE OF CHEMISTRY   (China)

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ARTICLE;

EID: 0000275083     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015990n     Document Type: Article

References (18)

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2. See: Williams, J. M.; Ferraro, J. R.; Thorn, R. J.; Carlson, K. D.; Geiser, U.; Wang, H. H.; Kini, A. M.; Whangbo, M.-H. Organic Superconductors (including Fullerenes); Prentice Hall: Englewod Cliffs, NJ, 1992.
3. (a) Bechgaard, K.; Cowan, D. O.; Bloch, A. N. J. Org. Chem. 1975, 40, 746.
4. (b) Engler, E. M.; Scott, B. A.; Etemad, S.; Penney, T.; Patel, V. V. J. Am. Chem. Soc. 1977, 99, 5909.
5. (c) Kini, A. M.; Parakka, J. P.; Geiser, U.; Wang, H.-H.; Rivas, F.; DiNino, E.; Thomas, S.; Dudek, J. D.; Williams, J. M. J. Mater. Chem. 1999, 9, 883.
6. (d) Li, H.-X.; Zhang, D.-Q.; Zhang, B.; Yao, Y.-X.; Xu, W.; Zhu, D.-B.; Wang, Z.-M. J. Mater. Chem. 2000, 10, 2063.
7. Svenstrup, N.; Becher, J. Synthesis 1995, 215, and further references therein.
8. (a) Falsig, M.; Lund, H. Acta Chem. Scand. B 1980, 34, 591.
9. (b) Wawzonek, S.; Heilmann, S. M. J. Org. Chem. 1974, 39(4), 511.
10. Morikami, T. A.; Otsubo, T. Synlett 1997, 319.
11. 4. This dichloromethane solution was decolorized by heating with activated charcoal. Column chromatography of the crude product after removing the solvents on silica gel with ethyl acetate afforded compound 3a as a yellow solid (0.70 g. 60%) and 1a as a yellow solid (6.7 mg, 4%).
12. 12N2S5: C, 47.34; H, 3.18; N, 7.36. Found: C, 46.95; H, 3.08; N, 7. 12.
13. -3. A total of 2152 observed reflections [I > 2σ(I)] and 130 variable parameters converged to R = 0.0357 and wR = 0.1062.
14. 2] dissolved in 15 mL of acetonitrile was mixed with this dense liquid, and the solution was stirred at 50-60 °C for 1.5-2 h. The reaction mixture was filtered, and the solid residue was washed twice with dichloromethane (20 mL). The combined filtrate and washings were decolorized by activated charcoal. After removing the solvent, column chromatography of the crude reaction mixture on silica gel with ethyl acetate/methanol (10:1) afforded compound 1a as a yellow solid (85.5 mg, 75%).
15. -3. A total of 5037 observed reflections [I > 2σ(I)] and 397 variable parameters converged to R = 0.0384 and wR = 0.1007.
16. (a) Galloway, C. P.; Doxsee, D. D.; Fenske, D.; Rauchfuss, T. B.; Wilson, S. R.; Yang, X. Inorg. Chem. 1994, 33, 4537.
17. (b) Chou, J.-H.; Rauchfuss, T. B.; Szczepura, L. F. J. Am. Chem. Soc. 1998, 120, 1805.
18. 2] (568.3 mg, 0.6 mmol) in 15 mL of acetonitrile were added 0.2 mL (2.4 mmol) of 3-bromopropionitrile and 279.66 mg (2.4 mmol) of pyridine hydrochloride. The mixture was heated to 50-60 °C and stirred for 2 h at this temperature. The resulting mixture was filtered ho, and the remaining solid was further washed with dichloromethane (3 x 20 mL) for complete extraction of the product. The combined filtrate and washings were decolorized by use of activated charcoal. After removing the solvent, column Chromatography of the crude reaction mixture on silica gel with dichloromethane afforded compound 3d as a yellow solid (184 mg 70%) and 1d (62 mg, 17%).