(1,3-Dithiolan-2-yl)trimethylammonium Iodide. An Electrophilic Dithiolanylating Reagent
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概要
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The reactions of (1,3-dithiolan-2-yl)trimethylammonium iodide (<B>5</B>), readily obtained by methylation of 2-dimethylamino-1,3-dithiolane (<B>2</B>), with aromatic amines were studied. It was found that <B>5</B> served as an electrophilic 1,3-dithiolanylating reagent; the reactions with aniline, <I>N</I>-methylaniline, and benzylamine gave <I>N</I>-dithiolanylated products while those with <I>N</I>,<I>N</I>-dimethylaniline and indole yielded exclusively <I>C</I>-dithiolanylated products <I>via</I> aromatic substitutions. Furthermore, <I>C</I>-dithiolanylated compounds were hydrolyzed to aldehydes using HgO–BF<SUB>3</SUB>·OEt<SUB>2</SUB>. The present aldehyde synthesis has been compared with an alternative electrophilic formylation method the Vilsmeier reaction.
- 公益社団法人 日本化学会の論文
著者
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Okawara Makoto
Research Laboratory Of Resources Utilization Tokyo Institute Of Technology
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Hiratani Kazuhisa
Research Laboratory of Resources Utilization, Tokyo Institute of Technology
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Nakai Takeshi
Research Laboratory of Resouces Utilization, Tokyo Institute of Technology
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- (1,3-Dithiolan-2-yl)trimethylammonium Iodide. An Electrophilic Dithiolanylating Reagent