128889-76-9Relevant academic research and scientific papers
Synthesis of 3-hydroxythiophenes and thiophen-3(2H)-ones by pyrolysis of alkylsulfanylmethylene Meldrum's acid derivatives
Hunter, Gordon A.,McNab, Hamish
, p. 1209 - 1214 (2007/10/02)
3-Hydroxythiophene 1 and a range of its 2-substituted, 2,2-disubstituted and 5-substituted derivatives have been made by flash vacuum pyrolysis (FVP) of an appropriate alkylsulfanylmethylene derivative of Meldrum's acid 3 or 4.These compounds are readily obtained, either by reaction of methoxymethylene Meldrum's acid with alkylthiols in refluxing acetonitrile, or via the bis(methylsulfanyl) compound 18 by known procedures.The pyrolysis proceeds by a hydrogen-transfer-cyclisation mechanism in which thereis extensive loss of configuration of a chiral centre at the reaction site.The NMR and mass spectra of the Meldrum's acid precursors and the mass spectra of the 3-hydroxythiophenes are briefly discussed.
