The first examples of selective carbonylation of n-butane and n-pentane

被引:15
作者
Akhrem, I [1 ]
Orlinkov, A [1 ]
Afanas'eva, L [1 ]
Petrovskii, P [1 ]
Vitt, S [1 ]
机构
[1] AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia
基金
俄罗斯基础研究基金会;
关键词
D O I
10.1016/S0040-4039(99)01125-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The polyhalomethane based superelectrophilic systems allowed us to accomplish the first efficient and selective carbonylation of n-butane and n-pentane with CO. Depending on the nature of the superelectrophilic system, Me3CCOOR or EtCH(Me)COOR (R = H, Alk) can be obtained at -20 degrees C, I atm from n-butane and CO after water (or alcohol) treatment in approximate to 90% yield based on the superelectrophilic system. Pentane reacts with CO in the presence of the CBr4. 2AlBr(3) superacid to give a single product, EtC(Me)(2)COOR, in almost quantitative yield. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5897 / 5900
页数:4
相关论文
共 13 条
[1]   An effective formylation of adamantane with CO initiated by the aprotic organic superacid CBr4 center dot 2AlBr(3) under mild conditions [J].
Akhrem, I ;
Churilova, I ;
Bernadyuk, S ;
Volpin, M .
TETRAHEDRON LETTERS, 1996, 37 (32) :5775-5778
[2]   A NOVEL FAMILY OF APROTIC ORGANIC SUPERACIDS FOR LOW-TEMPERATURE ALKANE AND CYCLOALKANE TRANSFORMATIONS [J].
AKHREM, I ;
ORLINKOV, A ;
VOLPIN, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (08) :671-672
[3]   Functionalization of saturated hydrocarbons by aprotic superacids .6. Effective regioselective monoformylation of adamantane in the presence of a hydride ion donor [J].
Akhrem, IS ;
Churilova, IM ;
Vitt, SV ;
Orlinkov, AV ;
Volpin, ME .
RUSSIAN CHEMICAL BULLETIN, 1997, 46 (03) :491-495
[4]   Functionalization of saturated hydrocarbons by aprotic superacids .5. Regioselective carbonylation of propane in an organic solvent initiated by aprotic organic superacids CX(4)center dot nAlBr(3) (X=Br,Cl; n=1 or 2) [J].
Akhrem, IS ;
Orlinkov, AV ;
Afanaseva, LV ;
Volpin, ME .
RUSSIAN CHEMICAL BULLETIN, 1996, 45 (05) :1154-1156
[5]  
AKHREM IS, 1993, MENDELEEV COMMUN, P188
[6]   Novel superelectrophilic complexes for low-temperature alkane and cycloalkane transformations [J].
Akhrem, IS ;
Orlinkov, AV .
RUSSIAN CHEMICAL BULLETIN, 1998, 47 (05) :740-764
[7]  
BALABAN AT, 1959, LIEBIGS ANN CHEM, V625, P66
[8]  
BERNADYUK SZ, 1994, MENDELEEV COMMUN, P183
[9]  
Hogeveen H., 1973, ADV PHYS ORG CHEM, V10, P29
[10]  
HOPFF H, 1936, BER, V69, P2241