Synthesis of phosphonium salts under microwave activation - Leaving group and phosphine substituents effects

被引:24
作者
Cvengros, J
Toma, S
Marque, S
Loupy, A
机构
[1] Univ Paris 11, Inst Chim Mol & Mat Orsay, CNRS, UMR 8615,Lab React Select Supports, F-91405 Orsay, France
[2] Comenius Univ, Fac Nat Sci, SK-84215 Bratislava, Slovakia
关键词
microwave irradiation; specific effects; phosphonium salts; leaving group effects;
D O I
10.1139/V04-103
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The specific nonpurely thermal effects of microwaves were evidenced according to neutral or charged leaving groups during nucleophilic substitution of benzylic electrophiles with triphenylphosphine and tributylphosphine. Microwave (MW) irradiation considerably enhanced the reactions with charged alkylating agents, especially under solvent-free conditions. Results are interpreted considering the magnitude of MW effects according to the position of the transition state along the reaction coordinates.
引用
收藏
页码:1365 / 1371
页数:7
相关论文
共 45 条
[1]  
[Anonymous], [No title captured]
[2]  
[Anonymous], MICROWAVES ORGANIC S
[3]   SCOPE AND MECHANISM OF REACTION OF ALKYLIDENEPHOSPHORANES WITH NITRILES [J].
BARNHARD.RG ;
MCEWEN, WE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (26) :7009-+
[4]   ORGANIC-SYNTHESIS IN MICROWAVE FIELD - 1ST EXAMPLE OF SPECIFIC ACTIVATION UNDER HOMOGENEOUS CONDITIONS [J].
BERLAN, J ;
GIBOREAU, P ;
LEFEUVRE, S ;
MARCHAND, C .
TETRAHEDRON LETTERS, 1991, 32 (21) :2363-2366
[5]   STUDIES ON THE SYNTHESIS OF LINEAR ALIPHATIC-COMPOUNDS .3. THE SYNTHESIS OF PARAFFINS WITH VERY LONG CHAINS [J].
BIDD, I ;
HOLDUP, DW ;
WHITING, MC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (11) :2455-2463
[6]   Microwave-assisted oxidation of alcohols using Magtrieve™ [J].
Bogdal, D ;
Lukasiewicz, M ;
Pielichowski, J ;
Miciak, A ;
Bednarz, S .
TETRAHEDRON, 2003, 59 (05) :649-653
[7]   MICROWAVE-ASSISTED ORGANIC-REACTIONS [J].
CADDICK, S .
TETRAHEDRON, 1995, 51 (38) :10403-10432
[8]   Synthesis of new diols derived from dianhydrohexitols ethers under microwave-assisted phase transfer catalysis [J].
Chatti, S ;
Bortolussi, M ;
Loupy, A .
TETRAHEDRON, 2000, 56 (32) :5877-5883
[9]   Equilibrium acidities and homolytic bond dissociation enthalpies of the acidic C-H bonds in As-substituted triphenylarsonium and related cations [J].
Cheng, JP ;
Liu, B ;
Zhao, YY ;
Zhang, XM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :7072-7077
[10]   Improved preparations of ionic liquids using microwave irradiation [J].
Deetlefs, M ;
Seddon, KR .
GREEN CHEMISTRY, 2003, 5 (02) :181-186