The intramolecular carbolithiation of vinyl sulfides at –105 °C in THF has been found to be stereospecific regarding the formation of the new carbon–carbon bond and non stereospecific regarding the formation of the new carbon–lithium bond. The resulting α-durylthioalkyllithium compounds are configurationally stable at –105 °C and epimerize at –90 °C.
R. W. Hoffmann, R. Koberstein and K. Harms, J. Chem. Soc., Perkin Trans. 2, 1999, 183 DOI: 10.1039/A808116F
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