Synlett

A Mild Synthesis of Nitriles by von Braun Degradation of Amides Using Triphenyl Phosphite-Halogen-Based Reagents

D Vaccari, P Davoli, A Spaggiari, F Prati

Index: Vaccari, Daniele; Davoli, Paolo; Spaggiari, Alberto; Prati, Fabio Synlett, 2008 , # 9 p. 1317 - 1320

Full Text: HTML

Citation Number: 6

Abstract

Abstract A mild procedure for the synthesis of aromatic and aliphatic nitriles is disclosed. In the presence of bromotriphenoxyphosphonium bromide (TPPBr 2), N-alkyl and N, N-dialkyl amides undergo von Braun degradation to nitriles in good to excellent yields under the mildest conditions ever reported. The reaction proceeds via formation of an iminoyl bromide intermediate at-60 C, which subsequently dealkylate upon refluxing in chloroform or even ...

 Related Synthetic Route

~62%

Learn More

~89%

Learn More

~94%

Learn More

~69%

Learn More

~91%

Learn More

~62%

Learn More

~55%

Learn More

~53%

Learn More

~67%

Learn More

~68%

Learn More

~88%

Learn More

~60%

Learn More

~93%

Learn More

~99%

Learn More

~95%

Learn More

~82%

Learn More

~71%

Learn More

~65%

Learn More

~52%

Learn More

~48%

Learn More

~39%

Learn More

~%

Learn More