Tri(hetero)substituted Carbonium Ions. I. Neighboring-Group Participation of the <I>N</I>,<I>N</I>-Dimethyldithiocarbamate Function Involving the Intermediacy of 2-Dimethylamino-1,3-dithiolanylium Ion
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概要
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The equimolar reaction of 1,2-dichloroethane with sodium <I>N</I>,<I>N</I>-dimethyldithiocarbamate was studied in various solvents. As major products, ethylene bis(<I>N</I>,<I>N</I>-dimethyldithiocarbamate) and 2-dimethylamino-l,3-dithiolanylium salt (the perchlorate or the tetraphenylborate) were obtained in yields, largely varying with the solvent used. On the basis of the solvent effect on the product ratio, and kinetic experiments it has been verified that neighboring-group participation of the <I>N</I>,<I>N</I>-dimethyldithiocarbamate function would be involved through the intermediacy of the isolated anchimeric carbonium ion, and that such participation is more predominant in nonpolar aprotic solvents such as dioxane and tetrahydrofuran. The mechanism of the reaction between 2-dimethylamino-l,3-dithiolanylium ion and the dithiocarbamate anion was established.
- 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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Ueno Yoshio
Research Institute For Biosciences And Department Of Toxicology And Microbial Chemistry Faculty Of Pharmaceutical Sciences Science University Of Tokyo
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Nakai Takeshi
Research Laboratory of Resources Utilization, Tokyo Institute of Technology
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