Evidence is presented indicating that 2,5-dimethoxythiophen is metallated in the β-position by butyl-lithium to give 2,5-dimethoxy-3-thienyl-lithium, which subsequently undergoes ring-opening. By the use of 2 equiv. of butyl-lithium followed by dimethyl sulphate, it was possible to isolate 1-methylthio-octa-1,3-diyne as the main product.
A. Hallberg, T. Frejd and S. Gronowitz, J. Chem. Soc., Perkin Trans. 1, 1980, 1390 DOI: 10.1039/P19800001390
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