New method for the synthesis of nitriles from O-arylaldoximes with ZrCl4

被引:12
作者
Tsuji, C [1 ]
Miyazawa, E [1 ]
Sakamoto, T [1 ]
Kikugawa, Y [1 ]
机构
[1] Josai Univ, Fac Pharmaceut Sci, Sakado, Saitama 3500295, Japan
关键词
O-aryloxime; nitrile; ZrCl4;
D O I
10.1081/SCC-120015406
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nitriles were readily synthesized from the corresponding O-phenyl- or O-(p-cyanophenyl)-aldoximes with ZrCl4 in nitromethane or in benzene.
引用
收藏
页码:3871 / 3879
页数:9
相关论文
共 14 条
[1]   NUCLEOPHILIC SUBSTITUTION IN THE BENZENE RING .1. RATES OF REACTIONS OF PARA-SUBSTITUTED BROMOBENZENES WITH PIPERIDINE [J].
BUNNETT, JF ;
LEVITT, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (08) :2778-2779
[2]   CONVENIENT SYNTHESIS OF O-PHENYLHYDROXYLAMINE [J].
CADOGAN, JIG ;
ROWLEY, AG .
SYNTHETIC COMMUNICATIONS, 1977, 7 (06) :365-366
[3]  
Friedrich K., 1970, CHEM CYANO GROUP, P7, DOI DOI 10.1002/9780470771242.CH2
[4]   A rare acid-promoted elimination of O-methyl oximes:: A practical synthesis of 3-cyano-4-benzopyrones [J].
Hsung, RP ;
Zificsak, CA ;
Wei, LL ;
Zehnder, LR ;
Park, F ;
Kim, M ;
Tran, TTT .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23) :8736-8740
[5]   A new method for the generation of nitriles from aldoximes [J].
Jose, B ;
Sulatha, MS ;
Pillai, PM ;
Prathapan, S .
SYNTHETIC COMMUNICATIONS, 2000, 30 (08) :1509-1514
[6]   A NEW SYNTHESIS OF NITRILES FROM N-METHOXY IMIDOYL BROMIDES BY PHOTOLYSIS [J].
KIKUGAWA, Y ;
FU, LH ;
SAKAMOTO, T .
SYNTHETIC COMMUNICATIONS, 1993, 23 (08) :1061-1069
[7]   A new intramolecular migration of the imino group of O-arylketoximes to the aryl group under the Beckmann condition [J].
Kikugawa, Y ;
Tsuji, C ;
Miyazawa, E ;
Sakamoto, T .
TETRAHEDRON LETTERS, 2001, 42 (12) :2337-2339
[8]   PARA-CYANOPHENOL FROM PARA-NITROBENZALDOXIME BY AN APPARENT DEHYDRATION-DISPLACEMENT, AND A SUGGESTED MODIFICATION OF MILLER-LOUDON CONVERSION OF ALDEHYDES TO NITRILES [J].
KNUDSEN, RD ;
MORRICE, AG ;
SNYDER, HR .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (20) :2878-2880
[9]  
Miller CP, 2000, SYNLETT, P1169
[10]   Preparation of ring-substituted phenoxylamine derivatives [J].
Miyazawa, E ;
Sakamoto, T ;
Kikugawa, Y .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1997, 29 (05) :594-600