A Sterically Congested [alpha]-Cyanoamine as a Cyanating Reagent: Cyanation of Acetals and Orthoesters

A Sterically Congested [alpha]-Cyanoamine as a Cyanating Reagent: Cyanation of Acetals and Orthoesters

The cyanation of acetals and orthoesters by using a sterically congested [alpha]-cyanoamine as a cyanating reagent was investigated. The [alpha]-cyanoamine effectively facilitated cyanation in the presence of trichlorosilyl triflate to produce a variety of cyanated adducts in excellent yields. Analy...

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Veröffentlicht in:European journal of organic chemistry 2015-10, Vol.2015 (30), p.6606
Hauptverfasser: Kotani, Shunsuke, Sakamoto, Midori, Osakama, Kazuki, Nakajima, Makoto
Format: Artikel
Sprache:eng
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Zusammenfassung:The cyanation of acetals and orthoesters by using a sterically congested [alpha]-cyanoamine as a cyanating reagent was investigated. The [alpha]-cyanoamine effectively facilitated cyanation in the presence of trichlorosilyl triflate to produce a variety of cyanated adducts in excellent yields. Analysis of the reaction mixture by 1H NMR spectroscopy revealed that trichlorosilyl triflate produced an oxocarbenium cation species as an intermediate.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201501084