Von Braun Degradation

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Fabio Prati - One of the best experts on this subject based on the ideXlab platform.

  • a mild synthesis of nitriles by Von Braun Degradation of amides using triphenyl phosphite halogen based reagents
    Synlett, 2008
    Co-Authors: Daniele Vaccari, Paolo Davoli, Alberto Spaggiari, Fabio Prati
    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 at room temperature. In the case of N- TERT-butyl, N-α-phenylethyl and N-benzhydryl amides, chlorotriphenoxyphosphonium chloride (TPPCl 2 ) generated at -30 °C was also effective.

Daniele Vaccari - One of the best experts on this subject based on the ideXlab platform.

  • a mild synthesis of nitriles by Von Braun Degradation of amides using triphenyl phosphite halogen based reagents
    Synlett, 2008
    Co-Authors: Daniele Vaccari, Paolo Davoli, Alberto Spaggiari, Fabio Prati
    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 at room temperature. In the case of N- TERT-butyl, N-α-phenylethyl and N-benzhydryl amides, chlorotriphenoxyphosphonium chloride (TPPCl 2 ) generated at -30 °C was also effective.

Alberto Spaggiari - One of the best experts on this subject based on the ideXlab platform.

  • a mild synthesis of nitriles by Von Braun Degradation of amides using triphenyl phosphite halogen based reagents
    Synlett, 2008
    Co-Authors: Daniele Vaccari, Paolo Davoli, Alberto Spaggiari, Fabio Prati
    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 at room temperature. In the case of N- TERT-butyl, N-α-phenylethyl and N-benzhydryl amides, chlorotriphenoxyphosphonium chloride (TPPCl 2 ) generated at -30 °C was also effective.

Paolo Davoli - One of the best experts on this subject based on the ideXlab platform.

  • a mild synthesis of nitriles by Von Braun Degradation of amides using triphenyl phosphite halogen based reagents
    Synlett, 2008
    Co-Authors: Daniele Vaccari, Paolo Davoli, Alberto Spaggiari, Fabio Prati
    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 at room temperature. In the case of N- TERT-butyl, N-α-phenylethyl and N-benzhydryl amides, chlorotriphenoxyphosphonium chloride (TPPCl 2 ) generated at -30 °C was also effective.

Jie Jack Li - One of the best experts on this subject based on the ideXlab platform.