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Synthesis 1989; 1989(2): 101-106
DOI: 10.1055/s-1989-27163
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Synthesis and Reactivity of Diethyl (Methylthio)(trimethylsilyl)methylphosphonate

Marian Mikołajczyk* , Piotr Bałczewski
  • *Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Organic Sulphur Compounds, PL-90-362 Łódź, Boczna 5, Poland
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Publication History

Publication Date:
17 September 2002 (online)

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The title compound is obtained in 80% yield by silylation of the lithium salt of diethyl 1-methylthiomethylphosphonate. Other approaches involving sulfenylation of diethyl 1-trimethylsilylmethylphosphonate or the Arbuzov reaction of triethyl phosphite with bromo(methylthio)(trimethylsilyl)methane are less efficient. Aldehydes react with the lithium salt of diethyl (methylthio)(trimethylsilyl)methylphosphonate to give the corresponding 1-methylthioethenylphosphonates in good yields (60-85%) while the reaction with ketones is more complex and Peterson reaction products are formed in very low yields. Methylation, silylation, sulfenylation, and oxidation of the title compound are also described.

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