A New Synthesis of Olefins via the Elimination Reaction of β-Tributylstannyl Organosulfur Compounds
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.
PHOTOCHEMISTRY OF AZOLES, PART VII. PHOTOSOLVOLYSIS OF ALKYLMERCAPTOAZOLES. AN APPLICATION TO SOME ACYCLIC MONOTERPENE DERIVATIVES
Salts derived from 2-alkylmercapto-1-methylimidazoles 1b-e and 3-alkylmercapto-4-methyl-1,2,4-triazoles 2b-d have been found to undergo photochemical heterolytic fission of the S-alkyl bond in aqueous or methanolic solution to give solvolysis-type products.
Iwasaki, Shigeo
p. 125 - 138
(2007/10/02)
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