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36). B T M A Br 3, aq N a O H R1--SO-R 2 R1--S--R 2 CHzC12 rt, or C1CH2CH2C1 reflux 47 - 98 % Fig. 28. Oxidation of sulfides to sulfoxides with BTMA Br 3 Although the oxidation of thiols with chlorine or bromine in the presence of water gives sulfonyl halides or sulfonic acids, the reaction of thiols with a stoichiometric amount of BTMA Br3 and sodium hydroxide in dichloromethanewater at room temperature gives disulfides in good yields (Fig. 29) (ref. 37). B T M A Br 3, aq N a O H 2 R--SH ~ CH2C12, rt, 10-20 min R--S--S--R 60-99 % Fig.

Recently, we also found that the reaction of primary amines and hydrazo compounds with BTMA Br 3 in aq. sodium hydroxide or in water gave corresponding nitriles and azo compounds in satisfactory yields, respectively (Fig. 27) (ref. 35). 5 - 10 h R-N-N-R 60-91% Fig. 27. Oxidation of primary amines and hydrazo compounds with BTMA Br3 43 Oxidation of sulfides to sulfoxides and oxidation of thiols to disulfides The oxidation of sulfides to sulfoxides are occasionally found to be unsatisfactory, since the resulting sulfoxides are easily oxidized to sulfones.

Yonemaru, S. Kajigaeshi, Nippon Kagaku Kaishi, 112 (1990). 13. J. Berthelot, C. Guette, M. Ouchefoune, P-L. Desbene, J-J. Basselier, J. Chem. Research (S), 381 (1986). 14. S. Kajigaeshi, T. Kakinami, M. Moriwaki, T. Tanaka, S. Fujisaki, T. Okamoto, Chem. Express, 3, 219 (1988). 15. S. Kajigaeshi, M. Moriwaki, T. Tanaka, S. Fujisaki, T. Kakinami, T. Okamoto, J. Chem. , Perkin Tram. I, 897 (1990). 16. S. Kajigaeshi, T. Kakinami, M. Moriwaki, T. Tanaka, S. Fujisaki, T. Okamoto, Bull. Chem. Soc. , 62, 439 (1989).

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