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