2- Alkylthiothiazoles, rearrangement

Alkylthiothiazoles rearrange thermally into the 3-alkylthiazoline-2-thiones in the imidazole series a thermal equilibrium is reached. 

Alkylthiothiazoles (114) when treated with catalytic amounts of iodine or of 2-methylthio-3-methylthiazolium salts 115 rearrange to the isomeric N-alkvl-A-4-thiazoline-2-thione (116) (Scheme 58). The... 

Like their oxygen analogues, 2-alkylthiothiazoles (220) rearrange to 3-alkyl-A4-thiazo-line-2-thiones (222) when heated with iodine, or preferably, with catalytic amounts of the corresponding quaternary salt (221 Scheme 150). The values of AH, AS and AG associated with this equilibrium measure the importance of steric interactions between R3 and R4 substituents in the A4-thiazoline-2-thione ring (Table 25). If 3-methyl-4-/-butyl-A4-thiazo-line-2-thione (223) is heated with the catalyst, the isomeric thioether (224) is formed in quantitative yield. 

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See also in sourсe #XX -- [ ]

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