Chiral organometallic reagents. Part XXIII. 1 On the stereochemistry of the carbolithiation reaction of vinyl sulfides

RW Hoffmann, R Koberstein, K Harms

Index: Hoffmann, Reinhard W.; Koberstein, Ralf; Harms, Klaus Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 2 p. 183 - 191

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Citation Number: 26

Abstract

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.