A mild synthesis of nitriles by von Braun degradation of amides using triphenyl phosphite-halogen-based reagents.

[摘要]：A mild procedure for the synthesis of arom. and aliph. nitriles is disclosed. In the presence of Br(PhO)3P+Br- (TPPBr2), N-alkyl and N,N-dialkyl amides undergo von Braun degrdn. 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? which subsequently dealkylates upon refluxing in CHCl3 or even at room temp. In the case of N-tert-Bu, N-a-phenylethyl, and N-benzhydryl amides, Cl(PhO)3P+Cl- (TPPCl2) generated at -30?was also effective.

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