Abstract
Thetin (1) and the betain of-Thiolanyl-acetic acid,5 react with the anhydrides of trifluoroacetic acid (TFA) and trichloroacetic acid (TClA), respectively, to give stable diacyl-S-ylides2a,b and6a,b, respectively. In contrast to the corresponding N-betaines,1 and5 react with monochloroacetic anhydride (MClA) under formation of the diacyl-ylid2c from1, and the mixed anhydride of chloroacetic acid and chloroacetylthiolaniummethylid carboxylic acid9 from5. The formation of9 requires the establishment of an equilibrium between S-betain and S-ylid forms. An X-ray analysis has been performed on2a.
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19. Mitt.:Ziegler E.,Wittmann H., Monatsh. Chem., im Druck.
Johnson A. W., Ylid Chemistry, S. 304ff. New York-London: Academic Press. 1966. Dort zitiert:Craig D. P., Magnusson E. A., J. Chem. Soc. (London)1956, 4895;Gillespie R. J., Robinson E. A., Can. J. Chem.41, 2074 (1963).
Wittmann H., Ziegler E., Monatsh. Chem.113, 1451 (1982).
Trost B. M., Melvin L. S. jr., Sulfur Ylides, S. 27. New York-San Francisco-London: Academic Press. 1975. Dort zitiert:Christensen A. T., Thom E., Acta Crystallogr., Sect.B27, 581 (1971);Christensen A. T., Witmore W. G., Acta Crystallogr. Sect.B25, 73 (1969).
Wittmann H., Beutel P., Ziegler E., Monatsh. Chem.100, 1362 (1969).
Hochrainer A.,Wessely F., Tetrahedron Lett.1965, 721.
Wittmann H., Ziegler E., Monatsh. Chem.112, 1333 (1981).
Ziegler E., Wittmann H., Peters K., Monatsh. Chem.114, 783 (1983).
Johnson A. W.,Amel R. T., Tetrahedron Lett.1966, 819.
Wittmann H., Ziegler E., Monatsh. Chem.114, 1223 (1983).
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Herrn Dr. Dr. h.c.Herbert Hönel, Graz, mit besten Wünschen zur Vollendung des 95. Lebensjahres gewidmet.
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Wittmann, H., Ziegler, E., Sterk, H. et al. Über Reaktionen mit Betainen, 20. Mitt. Synthesen stabiler S-Ylide. Monatsh Chem 116, 1189–1198 (1985). https://doi.org/10.1007/BF00811252
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DOI: https://doi.org/10.1007/BF00811252