Abstract
Photolysis of argon-matrix isolated 4,5-bis(carbomethoxy)-1,2,3-thiadiazole with λ = 254 or 265 nm resulted in the almost quantitative formation of bis(carbomethoxy)-thiirene (3g). Photolysis of 3g could only be carried out by long irradiation times at short wavelength λ = 210 nm and resulted mainly in extensive fragmentation instead of the formation of bis(carbomethoxy)thioketene, confirming earlier predictions that substituents, especially electron-withdrawing ones, should stabilize the thiirene ring. Methylcarboethoxy and methylacetylthioketene were obtained, however, in the argon-matrix photolysis or flow thermolysis of 4-methyl-5-carboethoxy-or 4-carboethoxy-5-methyl-1,2,3-thiadiazole and 4-acetyl-5-methyl-1,2,3-thiadiazole, respectively.
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