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Rhodium-Catalyzed Isomerization and Alkyne Exchange Reactions of 1,4-Dithiins via the 1,2-Ethenedithiolato Rhodium Complex
Arisawa, Mieko,Sawahata, Kyosuke,Ichikawa, Takuya,Yamaguchi, Masahiko
, p. 3174 - 3180 (2018/09/25)
Rhodium-catalyzed isomerization and alkyne exchange reactions of 1,4-dithiines occurred by cleavage of two C-S bonds. The 2,5- and 2,6-disubstituted 1,4-dithiins underwent isomerization reactions in toluene at 110 °C, providing equilibrium mixtures of isomers. At 150 °C, the reaction of 1,4-dithiins and dimethyl acetylenedicarboxylate gave unsymmetric 2,3-di(methoxycarbonyl)-1,4-dithiins and 2,3-di(methoxycarbonyl)thiophenes, the latter of which were formed by desulfurization of the 1,4-dithiins. A related reaction of the alkyne and a 1,2-dithiete gave a 2,3-di(methoxycarbonyl)thiophene. These reactions are considered to involve 1,2-ethenedithiolato rhodium intermediates.
