31819-38-2Relevant academic research and scientific papers
Anodic Methoxylation of 2,5-Dimethyl- and Tetramethyl-thiophene. Formation and Transformation of 2,5-Dimethoxy Adducts
Yoshida, Kunihisa,Takeda, Kazusada,Fueno, Takayuki
, p. 2817 - 2820 (2007/10/02)
The electrooxidation of 2,5-dimethyl- and tetramethyl-thiophene in methanol containing sodium methoxide produced isomeric mixtures (in either case 40percent cis, 60percent trans) of the corresponding 2,5-dimethoxy adducts each in 30percent yield, together with side-chain oxidation products.During GLC analysis a portion of the 2,5-dimethoxy adduct of 2,5-dimethylthiophene loses a methanol molecule to give 2,5-dihydro-2-methoxy-2-methyl-5-methylenethiophene.By contrast, the 2,5-dimethoxy adduct of the tetramethyl compound remained intact to GLC.In CDCl3 solution in an NMR tube, each isomer of the 2,5-dimethoxy adducts was transformed into the corresponding 2-(methoxymethyl)thiophene.When sodium acetate was used as electrolyte, the products were the corresponding 2-(methoxymethyl)thiophenes plus thiophene-2-carbaldehydes.In order to synthesize 2-acetoxymethyl-5-methylthiophene as a reference compound, anodic acetoxylation of 2,5-dimethylthiophene was also examined.
