Silylation as a new strategy of the use of aliphatic nitro compounds in organic synthesis

被引:18
作者
Tartakovsky, VA [1 ]
Ioffe, SL [1 ]
Dilman, AD [1 ]
Tishkov, AA [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
关键词
aliphatic nitro compounds; silylation; organic synthesis; elimination; cyclization; cross-coupling; cycloaddition; silyl nitronates; N; N-bis(silyloxy)enamines; conjugated nitrosoalkenes; oximes; ene oximes; ene nitriles;
D O I
10.1023/A:1015056024675
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Silylation of aliphatic nitro compounds is considered as a versatile multistage process. Due to activation of the beta- and gamma-carbon atoms of the initial nitro substrates, these reactions give rise to a series of products untypical of the traditional chemistry of nitro compounds. A new redox process proposed in the present study involves controlled incomplete reduction of the nitro group with simultaneous oxidation of the carbon skeleton of the initial aliphatic nitro compound.
引用
收藏
页码:1936 / 1948
页数:13
相关论文
共 38 条
[1]   Nitro and related compounds [J].
Adams, JP ;
Box, DS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (07) :749-764
[2]   Nitro and related compounds [J].
Adams, JP ;
Paterson, JR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (22) :3695-3705
[3]   REAGENTS AND SYNTHETIC METHODS .65. THE NEF REACTION ON TRIALKYLSILYL NITRONATES PROMOTED BY M-CHLOROPERBENZOIC ACID - AN EFFICIENT ROUTE TO ALPHA-ALKOXYKETONES FROM NITROALKANES [J].
AIZPURUA, JM ;
OIARBIDE, M ;
PALOMO, C .
TETRAHEDRON LETTERS, 1987, 28 (44) :5361-5364
[4]  
Bliznets IV, 2000, MENDELEEV COMMUN, P142
[5]  
BLIZNETS IV, 2000, 8 BELG ORG SYNTH S G, P29
[6]   Chemistry of N,N-bis(silyloxy)enamines.: 3.: N,N-bis(silyloxy)enamines as β-C-nucleophiles in reaction with acetals mediated by trimethylsilyl trifluoromethanesulfonate [J].
Dilman, AD ;
Lyapkalo, IM ;
Ioffe, SL ;
Strelenko, YA ;
Tartakovsky, VA .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) :8826-8829
[7]  
Dilman AD, 1997, MENDELEEV COMMUN, P133
[8]  
Dilman AD, 1999, SYNTHESIS-STUTTGART, P1767
[9]  
Dilman AD, 1998, SYNTHESIS-STUTTGART, P181
[10]   Trimethylsilyl derivatives of aliphatic nitro compounds in α,β-C,C-cross-coupling [J].
Dilman, AD ;
Lyapkalo, IM ;
Ioffe, SL ;
Strelenko, YA ;
Tartakovsky, VA .
RUSSIAN CHEMICAL BULLETIN, 2000, 49 (05) :874-878