Nitrile oxides of the thiophene series: influence of steric factors on stability and reactivity in reactions of 1,3-dipolar cycloaddition
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The synthesis of a series of di- and trialkyl-substituted thiophenecarbonitrile oxides is described. Their addition to styrene is studied together with the quantitative evaluation of the influence of different alkyl groups on the rate of the 1,3-dipolar cycloaddition reaction by the method of competing reactions.
KeywordsOxide Organic Chemistry Nitrile Styrene Alkyl Group
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- 1.M. M. Krayushkin, M. A. Kalik, V. K. Zav'yalova, and V. S. Bogdanov, Khim. Geterotsikl. Soedin., No. 3, 403 (1988).Google Scholar
- 2.C. Grundmann and P. Grünanger, The Nitrile Oxides, Springer-Verlag, Berlin (1971).Google Scholar
- 3.H. Hartough, Thiophene and Its Derivatives, Interscience, New York (1952).Google Scholar
- 4.O. P. Yeaze, S. A. Harris, H. J. Heller, W. Johncock, S. N. Oliver, P. J. Strydom, and J. Whittall, J. Chem. Soc., Perkin 1, No. 5, 957 (1985).Google Scholar
- 5.N. Messina and E. V. Brown, J. Am. Chem. Soc., 74, 920 (1952).Google Scholar
- 6.L. I. Belen'kii and A. P. Yakubov, Tetrahedron, 40, 2471 (1984).Google Scholar
- 7.H. Wynberg and V. E. Wiersum, J. Org. Chem., 30, 1058 (1965).Google Scholar
- 8.I. A. Lee, Synthesis, No. 6, 508 (1982).Google Scholar
- 9.A. Russell, Investigation of Rates and Mechanisms of Reactions. Part 2, Interscience, New York (1961), p. 344.Google Scholar
- 10.P. Cagniant, G. Merle, and D. Cagniant, Bull. Soc. Chim. France, No. 1, 302 (1970).Google Scholar