Reaction of α-Chloro Sulfoxides with Carbonyl and Thiocarbonyl Compounds
スポンサーリンク
概要
- 論文の詳細を見る
Ghloromethyl methyl sulfoxide undergoes a Darzens-type reaction with carbonyl compounds in the presence of potassium <I>t</I>-butoxide in <I>t</I>-butanol to afford methylsulfinyloxirane derivatives. The stereochemistry of this reaction has been studied. The reaction with a symmetrical ketone appeared to proceed stereospecifically to give only one isomer. On the other hand, the reaction with unsymmetrical ketones such as pinacolone or acetophenone produced a mixture of two diastereoisomers, in which a thermodynamically unstable isomer was predominant. The reaction with thiobenzophenone gave 1,1-diphenyl-2-methylsulfinylethylene which seems to have been formed from the intermediacy of 2,2-diphenyl-3-methylsulfinylthiirane. Mechanisms of these reactions are also discussed.
- 公益社団法人 日本化学会の論文
著者
-
TSUCHIHASHI Gen-ichi
Sagami Chemical Research Center
-
Ogura Katsuyuki
Sagami Chemical Research Center
関連論文
- A Convenient Synthesis of Methyl Methylthiomethyl Sulfoxide
- A new synthesis of arylacetic esters starting from aromatic aldehyde by the use of methyl (methylthio)methyl sulfoxide.
- Oxidation of methyl (methylthio)methyl sulfoxide.
- Asymmetric Hydrolysis of Prochiral Diesters with Pig Liver Esterase. Preparation of Optically Active Intermediates for the Synthesis of ( + )-Biotin and (+)-α-Methyl-3, 4-dihydroxyphenylalanine
- Thiocarbonyl Compounds as Potential Scavengers of Carbon Radicals
- Stereospecific reductive desulfinylation of 1-aryl-2-(methylsulfinyl)-2-(methylthio)ethenes with Grignard reagents.
- Synthesis of (S,S)-2-amino-3-phenylbutyric acid.
- The α-Chlorination of Sulfoxides with N-Chlorosuccinimide
- Reaction of α-Chloro Sulfoxides with Carbonyl and Thiocarbonyl Compounds
- Rearrangement of Aryl Sulfides in the Presence of Aluminum Chloride