A Sterically Congested α-Cyanoamine as a Cyanating Reagent: Cyanation of Acetals and Orthoesters

DOI: 10.1002/ejoc.201501084

Source and publish data:

European Journal of Organic Chemistry p. 6606 - 6609 (2015)

Update date:2022-09-26

Topics: Cyanation Acetals Sterically congested

Authors:

Kotani, Shunsuke

Sakamoto, Midori

Osakama, Kazuki

Nakajima, Makoto

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Article abstract of DOI:10.1002/ejoc.201501084

The cyanation of acetals and orthoesters by using a sterically congested α-cyanoamine as a cyanating reagent was investigated. The α-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.

Full text of DOI:10.1002/ejoc.201501084

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