A New Synthesis of Olefins via the Elimination Reaction of β-Tributylstannyl Organosulfur Compounds

Abstract

Organosulfur compounds on treatment with butyllithium in tetrahydrofuran followed by tributylstannylmethyl iodide 1 afforded olefins. The reaction was found to proceed via the destannylsulfurization of the initially formed β-stannyl organosulfur compounds. Thus, allyl 2-pyridyl sulfides 2 or allyl phenyl sulfones 12 were converted into 1, 3-dienes 4. Compounds 13 and 15 were converted into the olefins 14 and 17. Furthermore, the reaction was applied to the synthesis of α-substituted vinyl sulfides 24 and allene 27. The stereochemistry of the double bond is discussed.