19595-23-4Relevant academic research and scientific papers
A direct and stereoretentive synthesis of amides from cyclic alcohols
Mondal, Deboprosad,Bellucci, Luca,Lepore, Salvatore D.
, p. 7057 - 7061 (2012/01/03)
Chlorosulfites prepared in situ using thionyl chloride react with nitrile complexes of titanium(IV) fluoride to give a one-pot conversion of alcohols into amides. For the first time, amides are obtained from cyclic alcohols with stereoretention. Critical to the design of these new TiIV reactions has been the use of little-explored TiIV nitrile complexes that are thought to chelate chlorosulfites in the transition state tocreate a carbocation that is rapidly captured by the nitrile nucleophile through a front-side attack mechanism.
