Reaction of α-Halosulfoxides with Amines

スポンサーリンク

概要

• 論文の詳細を見る

• When optically active bromomethyl <I>p</I>-toly sulfoxide was treated with sodium methylmercaptide or sodium ethoxide, optically active α-substituted methyl <I>p</I>-toly sulfoxides were obtained in good yields. By contrast, reaction with secondary amines produced achiral <I>p</I>-toluenesulfenamides, methylenediamines, and amine hydrobromides in nearly quantitative yields. The reaction with an amine is presumed to proceed through the initial nucleophilic substitution at α-carbon of the sulfoxide to form aminomethyl <I>p</I>-toly sulfoxide, followed by rearrangement to the corresponding sulfenate, and subsequent attack of the amine at the sulfur atom of the sulfenate to form the final product. Meanwhile, a facile interconversion of alkoxymethyl <I>p</I>-toly sulfoxide and corresponding sulfenate was also observed.

• 公益社団法人 日本化学会の論文

著者

• Numata Tatsuo

  Department of Applied Chemistry, Faculty of Engineering, Osaka City University

関連論文

• Oxidative S-dealkylation reaction of sulfide catalyzed by Co(II)(bzacen).
• Enzymatic oxidation of alkyl sulfides by cytochrome P-450 and hydroxyl radical.
• Mechanism of the Oxygen Exchange Reaction of n-Butyl Methyl Sulfoxide in Sulfuric Acid
• Reaction of α-Halosulfoxides with Amines

スポンサーリンク