Catalytic Rearrangement of O, S-Dialkyl Dithiocarbonates to S, S-Dialkyl Dithiocarbonates by Pyridine N-Oxides.The Reaction Mechanism
スポンサーリンク
概要
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The reaction of O-alkyl S-methyl dithiocarbonates (xanthates) (I) with pyridine N-oxides (II) gave the corresponding S-alkyl S-methyl dithiocarbonates (dithiolcarbonate) (III) together with the symmetric S, S-dialkyl and S, S-dimethyl dithiocarbonates in good yieds. Pyridine N-oxides bearing electron-donating substituents are efficient catalysts for rearrangement of I to III.The reaction is pseudo-first-order and the apparent first-order rate constant is proportional to the concentration of II.The role of pyridine N-oxides and the reaction behavior of O, S-dialkyl dithiocarbonates are discussed on the basis of kinetic and molecular orbital calculation data.The rearrangement may proceed by nucleophilic attack of ^-SCOSR derived from a complex of I and II on the O-alkyl group of xanthates.The reaction provides a useful preparation method for alkanethiols by aminolysis of the products with ethanolamine.
- 公益社団法人日本薬学会の論文
- 1989-03-25
著者
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松岡 俊和
Faculty Of Pharmaceutical Sciences Kumamoto University
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原野 一誠
Faculty of Pharmaceutical Sciences, Kumamoto University
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久野 拓造
Faculty Of Pharmaceutical Sciences Kumamoto University
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原野 一誠
熊本大学 薬
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原野 一誠
熊本大学薬学部
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久野 拓三
熊本大学薬学部
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杉本 真一郎
Faculty Of Pharmaceutical Sciences Kumamoto University
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篠原 郁夫
Faculty of Pharmaceutical Sciences, Kumamoto University
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篠原 郁夫
Faculty Of Pharmaceutical Sciences Kumamoto University
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