92531-90-3Relevant academic research and scientific papers
A New Synthesis of Olefins via the Elimination Reaction of β-Tributylstannyl Organosulfur Compounds
Ochiai, Masahito,Ukita, Tatsuzo,Fujita, Eiichi,Tada, Shin-ichi
, p. 1829 - 1839 (2007/10/02)
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.Keywords - destannylsulfurization; allyl 2-pyridyl sulfide; allyl phenyl sulfone; synthesis of olefin; 1,3-diene; vinyl sulfide; β-tributylstannyl organosulfur compound.
