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
- 13Citations
- 11Captures
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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.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=45749107612&origin=inward; http://dx.doi.org/10.1055/s-2007-1072591; http://www.thieme-connect.de/DOI/DOI?10.1055/s-2007-1072591; http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2007-1072591.pdf; https://dx.doi.org/10.1055/s-2007-1072591; https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-2007-1072591
Georg Thieme Verlag KG
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