Trimethylsilyl cyanide promoted cyanation of tertiary alkyl chlorides and other 
SN1 active compounds

Reetz, Manfred T.; Chatziiosifidis, Ioannis; Künzer, Hermann; Müller-Starke, Hans

doi:10.1016/S0040-4020(01)88594-X

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Trimethylsilyl cyanide promoted cyanation of tertiary alkyl chlorides and other SN1 active compounds

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引用

Reetz, M. T., Chatziiosifidis, I., Künzer, H., & Müller-Starke, H. (1983). Trimethylsilyl cyanide promoted cyanation of tertiary alkyl chlorides and other SN1 active compounds. Tetrahedron, 39(6), 961-965. doi:10.1016/S0040-4020(01)88594-X.

引用: https://hdl.handle.net/21.11116/0000-000E-8307-6

要旨

Tertiary chlorides are readily cyanated in a one-pot procedure using trimethylsilyl cyanide in the presence of SnCl₄. The mechanism of this novel and synthetically useful reaction involves initial isonitrile formation followed by rearrangement to the tertiary nitrile. Other S_N1 active componds also undergo smooth cyanation.