PlumX Metrics
Embed PlumX Metrics

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

Synlett, ISSN: 0936-5214, Vol: 2008, Issue: 9, Page: 1317-1320
2008
  • 13
    Citations
  • 0
    Usage
  • 11
    Captures
  • 0
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    13
    • Citation Indexes
      13
  • Captures
    11

Article Description

A mild procedure for the synthesis of aromatic and aliphatic nitriles is disclosed. In the presence of bromotriphenoxyphosphonium bromide (TPPBr ), 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) generated at -30°C was also effective. © Georg Thieme Verlag Stuttgart.

Provide Feedback

Have ideas for a new metric? Would you like to see something else here?Let us know