A. Noack et al., RING TRANSFORMATIONS OF 4,5-DISUBSTITUTED TO THE ISOMERIC 3,4-DISUBSTITUTED ISOTHIAZOLIUM SALTS AND THEIR OXIDATION TO 1,1-DIOXIDES, Journal fur praktische Chemie, Chemiker-Zeitung, 340(4), 1998, pp. 361-366
4,5-Disubstituted N-phenyl-isothiazolium salts 1 with active 5-methyl
group react under the influence of anilines to form 3,4-disubstituted
isothiazolium salts 3. The influence of donor and acceptor substituent
s in the 2-phenyl group of 1a-h and in the anilines 2 on the ring tran
sformation were studied. The structure of the new salts was confirmed
by X-ray analysis. The 3-hydroperoxy-2,3-dihydro-isothiazole 1,1-dioxi
des (12a,d)and the isothiazole-3(2H) -one 1,1-dioxides (14a,d) are obt
ained by oxidation of salts 3 with H2O2.