Tosyl cyanide

Chemical properties

White powder

The Uses of Tosyl cyanide

Tosyl cyanide is used in a free-radical cyanation of B-alkylcatecholboranes. Also used as a component in a hetero-Diels-Alder reaction with 1,3-bis-silyl enol ethers leading to 4-hyroxypyridines.

The Uses of Tosyl cyanide

p-Toluenesulfonyl cyanide can be used in:

• The preparation of polyfunctional nitriles.
• Free-radical cyanation of B-alkylcatecholboranes.
• The synthesis of 4-hyroxypyridines by hetero-Diels-Alder reaction with 1,3-bis-silyl enol ethers.

What are the applications of Application

p-Toluenesulfonyl cyanide is used in the preparation of polyfunctional nitriles and free-radical cyanation of B-alkylcatecholboranes

Synthesis Reference(s)

Tetrahedron Letters, 10, p. 3351, 1969 DOI: 10.1017/S0009838800024678

General Description

p-Toluenesulfonyl cyanide is an electron-deficient nitrile. It undergoes hetero-Diels-Alder reaction with silyl enol ether of cyclohexenone to yield hydrolytically sensitive [4+2] adduct. It also undergoes facile [2+3] cycloaddition reaction with azides to form 5-sulfonyl tetrazoles. p-Toluenesulfonyl cyanide also reacts with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield sulfinates.