4-Cyano-3-oxotetrahydrothiophene (c-THT): An Ideal Acrylonitrile Anion Equivalent

Abstract

4-Cyano-3-oxotetrahydrothiophene (c-THT) has much more to offer than just a platform to various heterocyclic scaffolds. This solid, bench-stable and commercially available reagent can be readily transformed into thioglycolic acid and acrylonitrile upon simple addition of a hydroxide anion. This interesting feature enables its use as a particularly versatile acrylonitrile anion surrogate.

Keywords

• acrylonitrile
• surrogate
• heterocycle
• alkylation
• michael addition
• palladium
• retro-dieckmann