Tosyl cyanide
Product name: Tosyl cyanide
Synonym(s): p-Tolylsulfonyl cyanide
CAS Number: 19158-51-1
Introduction
| Appearance | White powder |
| Structure | Conforms to structure |
| Purity | ≥98% |
| Loss on drying | ≤0.5% |
General description
p-Toluenesulfonyl cyanide(CAS 19158-51-1) 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.
Application
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.
