The chemistry of acylals. Part II. Formation of nitriles by treatment of acylals with trimethylsilyl azide in the presence of a Lewis acid

被引:91
作者
Sandberg, M [1 ]
Sydnes, LK [1 ]
机构
[1] Univ Bergen, Dept Chem, N-5007 Bergen, Norway
关键词
acylals; azides; benzonitriles;
D O I
10.1016/S0040-4039(98)01309-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
When acylals from aliphatic and aromatic aldehydes are treated with trimethylsilyl azide in the presence of titanium(IV) chloride, the latter group of compounds is converted to the corresponding nitriles in good to excellent yields. By-products were not formed. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6361 / 6364
页数:4
相关论文
共 21 条
[1]  
GRUNDMANN C, 1965, METHODEN ORG CHEM 1, V10, P785
[2]   Acylals [J].
Hurd, CD ;
Green, FO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1941, 63 :2201-2204
[3]  
KIRCHMEYER S, 1983, SYNTHESIS-STUTTGART, P500
[4]   UNUSUAL REACTION FOR SUBSTITUTION OF ACETATE GROUP IN ACYLALS UNDER THE MAKOSZA CONDITIONS OF GENERATING DICHLOROCARBENE [J].
KRYSHTAL, GV ;
BOGDANOV, VS ;
YANOVSKAYA, LA ;
VOLKOV, YP ;
TRUSOVA, EI .
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1981, 30 (12) :2351-2354
[5]   AN UNUSUAL REACTION OF TRICHLOROMETHANE WITH ACYLALS IN THE INTERPHASE CATALYSIS CONDITIONS [J].
KRYSHTAL, GV ;
BOGDANOV, VS ;
YANOVSKAYA, LA ;
VOLKOV, YP ;
TRUSOVA, EI .
TETRAHEDRON LETTERS, 1982, 23 (35) :3607-3610
[6]  
KRYSHTAL GV, 1981, IAN SSSR KH, P2820
[7]   CLEAVAGE OF GEMINAL DIACETATES USING VARIOUS PHENOXIDES [J].
KU, YY ;
PATEL, R ;
SAWICK, D .
TETRAHEDRON LETTERS, 1993, 34 (50) :8037-8040
[8]  
Kyba EP., 1984, AZIDES NITRENES, P1
[9]   SYNTHESIS OF LONG-CHAIN ALKYL AZIDES AND THEIR AGGREGATION IN FORMAMIDE SOLUTIONS [J].
MARTI, MJ ;
RICO, I ;
ADER, JC ;
DESAVIGNAC, A ;
LATTES, A .
TETRAHEDRON LETTERS, 1989, 30 (10) :1245-1248
[10]   Carbon syntheses with malonic acid and related compounds. II. Aromatic aldehydes [J].
Michael, A ;
Weiner, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 :680-684