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
Full Text: HTML
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 ...
Related Articles:
Phosphonium salt-catalysed synthesis of nitriles from in situ activated oximes
[Denton, Ross M.; An, Jie; Lindovska, Petra; Lewis, William Tetrahedron, 2012 , vol. 68, # 13 p. 2899 - 2905]
[Nishiyama, Kozaburo; Oba, Makoto; Watanabe, Akio Tetrahedron, 1987 , vol. 43, # 4 p. 693 - 700]
[Deshmukh, Swapnil S.; Huddar, Sameerana N.; Jadhav, Ravindra R.; Akamanchi, Krishnacharya G. Tetrahedron Letters, 2011 , vol. 52, # 35 p. 4533 - 4536]
Facile transformation of esters to nitriles
[Suzuki, Yusuke; Moriyama, Katsuhiko; Togo, Hideo Tetrahedron, 2011 , vol. 67, # 41 p. 7956 - 7962]
[Ishii, Genki; Harigae, Ryo; Moriyama, Katsuhiko; Togo, Hideo Tetrahedron, 2013 , vol. 69, # 5 p. 1462 - 1469]