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

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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 ...

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~69%

~91%

~62%

~55%

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~67%

~68%

~88%

~60%

~93%

~99%

~95%

~82%

~71%

~65%

~52%

~48%

~39%

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