有機合成試薬「MT-スルホン」の化学 [in Japanese] Chemistry in Organic Synthesis Utilizing MT-Sulfone as a Reagent [in Japanese]
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Here, the preparative reactions, chemical reactivities, and synthetic utilization of MT-sulfone, a typical dithioacetal <I>S</I>, <I>S</I>-dioxide, are described. MT-sulfone, which is the abbreviation name of (methylthio) methyl <I>p</I>-tolyl sulfone, is conveniently prepared from DMSO in the so-called "one-pot" manner. The combination of methylthio group and <I>p</I>-tolylsulfonyl (tosyl) group contributes to the easy formation of a carbanion and a radical on the central carbon of dithioacetal <I>S</I>, <I>S</I>-dioxide functionality and realizes many types of reaction that transform the dithioacetal <I>S</I>, <I>S</I>-dioxide group into the desired functionalities. The C-C bond formation of MT-sulfone with a wide range of functional groups such as alkyl halides, aldehydes, and carboxylic esters makes synthetic intermediates, which are finally converted to the desired target molecules. Thus, MT-sulfone has proven to be a versatile reagent in organic synthesis. In this review, the synthetic methods using the ketene dithioacetal <I>S</I>, <I>S</I>-dioxides that can be easily derived from MT-sulfone are also surveyed.
- J. Synth. Org. Chem. Jpn.
J. Synth. Org. Chem. Jpn. 65(2), 90-98, 2007-02-01
The Society of Synthetic Organic Chemistry, Japan