Synthesis of alkyl and alkenyl furyl sulfoxides and their behavior in the pummerer reaction
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Oxidation of alkyl(alkenyl) furyl sulfides by hydrogen peroxide in glacial acetic acid affords alkyl(alkenyl) furyl sulfoxides, which react with acetic acid, acetic anhydride, and a mixture of acetic and trifluoroacetic anhydrides to give α-acyloxy-substituted and unsaturated sulfides as products, while for allyl 2-(5-methylfuryl) sulfoxide a thienofuran compound is obtained.
KeywordsOxidation Hydrogen Acetic Hydrogen Peroxide Sulfide
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- 1.S. Oae, Plenary Lecture on the 8th International Symposium on Organic Sulfur Chemistry, Yugoslavia (1978), p. 290.Google Scholar
- 2.E. N. Karaulova, in: Results of Science. Vol. 2: Chemistry of Oil and Gas [in Russian], Izd. AN SSSR, Moscow (1958), p. 130.Google Scholar
- 3.J. M. Maissant, J. M. Bodroux, C. Bouchele, and M. Braschar, J. Mol. Catal., 9, 237 (1980).Google Scholar
- 4.W. E. Parham and L. Edwards, J. Org. Chem., 33, 4150 (1968).Google Scholar
- 5.R. G. Aukharieva, T. A. Danilova, A. V. Anisimov, and E. A. Viktorova, Khim. Geterotsikl. Soedin., No. 5, 611 (1981).Google Scholar
- 6.A. V. Anisimov, V. F. Ionova, V. S. Babaitsev, V. K. Govorek, and E. A. Viktorova, Khim. Geterotsikl. Soedin., No. 8, 1062 (1979).Google Scholar
- 7.Ya. L. Gol'dfarb, Ya. L. Danyushevskii, and M. A. Vinogradova, Dokl. Akad. Nauk SSSR, 151, 332 (1963).Google Scholar
- 8.E. N. Karaulova, T. A. Bardina, G. D. Gal'pern, and T. S. Bobruiskaya, Neftekhim., 6, 480 (1966).Google Scholar
- 9.R. Tanikaga, Y. Yabuki, N. Ono, and A. Kaji, Tetrahedron Lett., No. 26, 2257 (1976).Google Scholar