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ChemInform Abstract: Addition of Grignard and Organolithium Reagents to the Negatively Charged Sulfur Atom of 2,2-Bis(diethylamino)ethan-2-ylium-1-dithioate.

✍ Scribed by J. NAKAYAMA; T. OTANI; Y. SUGIHARA; A. ISHII


Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis


Addition of Grignard and Organolithium Reagents to the Negatively Charged Sulfur Atom of 2,2-Bis(diethylamino)ethan-2-ylium-1dithioate.

-A range of organometal nucleophiles add to the negatively charged sulfur atom of the title betaine (I) despite the presence of the positively charged carbenium ion center. In situ methylation of the enethiolates thus formed provides dithioacetals in excellent yields. A mechanism involving a single-electron transfer process from nucleophiles to (I) is presented for this thiophilic addition. -(NAKAYAMA,


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