Abstract
Trimethylsilylpropynoic acid reacts with thionyl chloride to give a mixture of trimethylsilylpropynoyl chloride and 3-chloro-3-trimethylsilyl-2-propenoyl chloride whose ratio depends on the reaction conditions (temperature, reactant ratio). Dimethylformamide almost does not catalyze the reaction. Treatment of trimethylsilylpropynoic acid with oxalyl chloride in the presence of 0.04 equiv of DMF at room temperature ensures selective formation of trimethylsilylpropynoyl chloride (yield 80%).
Keywords
Chloride Organic Chemistry Dimethylformamide Reactant Ratio Thionyl
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
Preview
Unable to display preview. Download preview PDF.
REFERENCES
- 1.Patai, S., The Chemistry of Acyl Halides, New York: Wiley, 1972.Google Scholar
- 2.Clark, A.J., Al-Faiyz, V.S.S., Broadhurst, M.J., Patel, D., and Peacock, J.L., J. Chem. Soc., Perkin Trans. 1, 2000, p. 1117.Google Scholar
- 3.Black, D.A. and Arndtsen, B.A., Org. Lett., 2004, vol. 6, p. 1107.CrossRefGoogle Scholar
- 4.Xu, M., Giacomo, F., Paterson, D.E., George, T.G., and Vasella, A., Chem. Commun., 2003, p. 1452.Google Scholar
- 5.Jung, J.-C., Watkins, E.B., and Avery, M.A., Heterocycles, 2005, vol. 65, p. 77.Google Scholar
- 6.Kaboudin, B. and Navaee, K., Heterocycles, 2003, vol. 60, p. 2287.CrossRefGoogle Scholar
- 7.Britsun, V.N., Borisevich, A.N., Samoilenko, L.S., and Lozinskii, M.O., Russ. J. Org. Chem., 2005, vol. 41, p. 283.Google Scholar
- 8.Medvedeva, A.S., Russ. J. Org. Chem., 1996, vol. 32, p. 272.Google Scholar
- 9.Medvedeva, A.S., Kalikhman, I.D., and Vyazankin, N.S., Zh. Obshch. Khim., 1983, vol. 53, p. 1437.Google Scholar
- 10.Safronova, L.P., Medvedeva, A.S., and Vyazankin, N.S., Zh. Obshch. Khim., 1983, vol. 53, p. 1313; Medvedeva, A.S., Andreev, M.V., Safronova, L.P., Sarapulova, G.I., Pavlov, D.V., and Afonin, A.V., Russ. J. Org. Chem., 2002, vol. 38, p. 10; Safronova, L.P., Andreev, M.V., Afonin, A.V., and Medvedeva, A.S., Russ. J. Org. Chem., 2002, vol. 38, p. 788; Andreev, M.V., Medvedeva, A.S., Safronova, L.P., Afonin, A.V., and Sarapulova, G.I., Russ. J. Org. Chem., 2003, vol. 39, p. 1706.Google Scholar
- 11.Medvedeva, A.S., Safronova, L.P., Vyazankin, N.S., Voronkov, M.G., Andreeva, E.I., Fursenko, E.I., Ponomareva, E.E., Sanin, M.A., Andrianova, N.I., Gushchin, B.E., Chumakova, E.I., Erokhova, L.N., and Tsareva, I.S., USSR Inventor's Certificate no. 1531403, 1989; Byull. Izobret., 1989, no. 47; Safronova, L.P., Medvedeva, A.S., Vyazankin, N.S., Zaks, A.S., and Yushkov, V.V., USSR Inventor's Certificate no. 1048757, 1983; Byull. Izobret., 1983, no. 38.Google Scholar
- 12.Voronkov, M.G., Golovanova, N.I., Pukhnarevich, V.B., Shergina, N.I., and Yarosh, O.G., Dokl. Akad. Nauk SSSR, 1978, vol. 238, p. 874.Google Scholar
- 13.Proidakov, A.G., Kalabin, G.A., Golovanova, N.I., Pukhnarevich, V.B., Shergina, N.I., and Voronkov, M.G., Izv. Akad. Nauk SSSR. Ser. Khim., 1970, p. 462.Google Scholar
- 14.Medvedeva, A.S., Safronova, L.P., and Vyazankin, N.S., Zh. Obshch. Khim., 1980, vol. 50, p. 2044.Google Scholar
- 15.Urdaneta, N.A., Herrera, J.C., Salazar, J., and Lopez, S.E., Synth. Commun., 2002, vol. 32, p. 3003.CrossRefGoogle Scholar
- 16.Bowden, K. and Price, M.J., J. Chem. Soc., 1970, pp. 1466, 1472.Google Scholar
Copyright information
© MAIK "Nauka/Interperiodica" 2005