Application of lithium reagents from (1-methylthio) alkylphosphonate esters to the synthesis of ketones

EJ Corey, JI Shulman

Index: Corey,E.J.; Shulman,J.I. Journal of Organic Chemistry, 1970 , vol. 35, # 3 p. 777 - 780

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Citation Number: 142

Abstract

Diethyl methylthiomethylphosphonate can be alkylated by successive treatment with n- butyllithium and an n-alkyl iodide to give the corresponding (1-methy1thio) alkylphosphonate esters (4). The lithio derivatives of the latter (5) react with carbonyl compounds to form 8-alkoxy phosphonate adducts, which decompose upon heating to 50'(in tetrahydrofuran) to form substituted vinyl methyl sulfides (7). Ketones are obtained in good ...