塩化スルフィンイミドイルを用いる新しい酸化反応
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概要
- 論文の詳細を見る
Various alcohols are smoothly oxidized to the corresponding carbonyl compounds by using a stoichiometric amount of a new oxidant, <I>N-tert</I>-butylbenzenesulfinimidoyl chloride (1), in the coexistence of 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU). A new catalytic method mediated by a catalytic amount of 1 was further developed in order to solve the difficulties on purification of formed carbonyl compounds after this stoichiometric oxidation. That is, catalytic oxidation of various alcohols is efficiently performed by using a catalytic amount of <I>N-tert</I>-butylbenzenesulfenamide (2) and a stoichiometric amount of <I>N</I>-chlorosuccinimide (NCS). The catalytic oxidation is more useful than the above-mentioned stoichiometric one because of its wide applicability and efficiency. The new oxidant 1 efficiently dehydrogenates organic compounds other than alcohols. For example, ketones are smoothly dehydrogenated to α, β-unsaturated ketones at -78°Cin a one-pot manner by the reaction of lithium enolates of ketones and 1. Further, a variety of amines and hydroxylamines are also oxidized to the corresponding imines and nitrones, respectively, by using 1 and DBU under very mild conditions.
- 社団法人 有機合成化学協会の論文
- 2004-06-01