Halogen Addition to a Frustrated Lewis Pair

被引:18
作者
Froemel, Silke [1 ]
Froehlich, Roland [1 ]
Daniliuc, Constantin G. [1 ]
Kehr, Gerald [1 ]
Erker, Gerhard [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
关键词
Frustrated Lewis pairs; Phosphorus; Boron; Halogens; Zwitterions; FREE CATALYTIC-HYDROGENATION; HETEROLYTIC DIHYDROGEN ACTIVATION; SOLID-STATE; CRYSTAL-STRUCTURES; REAGENT PH3PCL2; ALKYL CHLORIDES; BORANE; PHOSPHINES; ALCOHOLS; BIS(PENTAFLUOROPHENYL)BORANE;
D O I
10.1002/ejic.201200288
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reactive intramolecular frustrated Lewis pair (FLP) Mes2PCH2CH2B(C6F5)2 reacts rapidly with thionyl chloride to yield the zwitterionic chlorination product [Mes2PCl+]CH2CH2[BCl(C6F5)2]. Analogous zwitterionic products were obtained by the reaction of the FLP with chlorine or bromine. Compounds [Mes2PX+]CH2CH2[BX(C6F5)2] (X = Cl, Br) were characterized by X-ray crystal structure analyses.
引用
收藏
页码:3774 / 3779
页数:6
相关论文
共 44 条
[1]   TERTIARY PHOSPHANE-TETRACHLOROMETHANE, A VERSATILE REAGENT FOR CHLORINATION, DEHYDRATION, AND P-N LINKAGE [J].
APPEL, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (12) :801-811
[2]  
Appel R., 1975, Angew. Chem, V87, P863
[3]   Structural relationships between o-, m- and p-tolyl substituted R3EI2 (E = As, P) and [(R3E)AuX] (E = As, P; X = Cl, Br, I) [J].
Barnes, Nicholas A. ;
Flower, Kevin R. ;
Godfrey, Stephen M. ;
Hurst, Paul A. ;
Khan, Rana Z. ;
Pritchard, Robin G. .
CRYSTENGCOMM, 2010, 12 (12) :4240-4251
[4]   Phosphine-Boranes and Related Ambiphilic Compounds: Synthesis, Structure, and Coordination to Transition Metals [J].
Bouhadir, Ghenwa ;
Amgoune, Abderrahmane ;
Bourissou, Didier .
ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 58, 2010, 58 :1-107
[5]   Capture of NO by a Frustrated Lewis Pair: A New Type of Persistent N-Oxyl Radical [J].
Cardenas, Allan Jay P. ;
Culotta, Brooks J. ;
Warren, Timothy H. ;
Grimme, Stefan ;
Stute, Annika ;
Froehlich, Roland ;
Kehr, Gerald ;
Erker, Gerhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7567-7571
[6]   Metal-free catalytic hydrogenation [J].
Chase, Preston A. ;
Welch, Gregory C. ;
Jurca, Titel ;
Stephan, Douglas W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (42) :8050-8053
[7]   The reaction of some tertiary phosphines with two mole equivalents of diiodine to produce the iodophosphonium triiodides [R3PI]I3;: influence of R in causing subtle variations in solid state structures [J].
Cross, WI ;
Godfrey, SM ;
McAuliffe, CA ;
Pritchard, RG ;
Sheffield, JM ;
Thompson, GM .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (16) :2795-2798
[8]   Catalytic Phosphorus(V)-Mediated Nucleophilic Substitution Reactions: Development of a Catalytic Appel Reaction [J].
Denton, Ross M. ;
An, Jie ;
Adeniran, Beatrice ;
Blake, Alexander J. ;
Lewis, William ;
Poulton, Andrew M. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16) :6749-6767
[9]  
DOWNIE IM, 1966, CHEM IND-LONDON, P900
[10]   Expanding the Scope of Metal-Free Catalytic Hydrogenation through Frustrated Lewis Pair Design [J].
Eros, Gabor ;
Mehdi, Hasan ;
Papai, Imre ;
Rokob, Tibor Andras ;
Kiraly, Peter ;
Tarkanyi, Gabor ;
Soos, Tibor .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (37) :6559-6563