77100-94-8Relevant academic research and scientific papers
Ligand exchange reaction of sulfoxides in organic synthesis: A versatile procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids and amides
Satoh, Tsuyoshi,Unno, Hideaki,Mizu, Yasuhiro,Hayashi, Yasumasa
, p. 7843 - 7854 (2007/10/03)
A novel two-step procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids and amides is described. Methylesters are reacted with lithium carbanion of chloromethyl phenyl sulfoxide to give α-chloro α-sulfinyl ketones in 70 to 90% yields. Potassium enolate of the α-chloro α-sulfinyl ketone was treated with tert-butyllithium at -78°C to give alkynolate via alkylidene carbenoid. This intermediate was treated with alcohols, thioles, 5% aqueous NaOH, and amine hydrochlorides to afford one-carbon homologated esters, thioesters, carboxylic acids and amides, respectively, in good to excellent yields.
NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS, 8. TRIMETHYLSILYLDIAZOMETHANE, A NEW, STABLE, AND SAFE REAGENT FOR THE CLASSICAL ARNDT-EISTERT SYNTHESIS
Aoyama, Toyohiko,Shioiri, Takayuki
, p. 4461 - 4462 (2007/10/02)
Stable and safe trimethylsilyldiazomethane (TMSCHN2) can be used efficiently for the Arndt-Eistert synthesis in place of highly toxic and explosive diazomethane.
