SINGLE ELECTRON-TRANSFER PROCESSES IN PERFLUOROALKYL HALIDES REACTIONS

被引:46
作者
WAKSELMAN, C
机构
[1] CNRS-CERCOA, 94320 Thiais
关键词
D O I
10.1016/S0022-1139(00)80331-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Reactions of nucleophiles, radical anions or metals with perfluoroalkyl bromides or iodides, which follow an electron-transfer (ET) mechanism, are reviewed. The nature of this step (classical, dissociative or associative ET) is not known with certainty. Proofs of the existence of an intermediate radical are based on inhibition and capture experiments. These reactions allow the preparation of fluorinated products, such as alpha-perfluoroalkyl ketones, perfluoroalkyl sulfides, perfluoroalkane sulfinates and perfluoroalkyl aromatic compounds.
引用
收藏
页码:367 / 378
页数:12
相关论文
共 36 条
[1]   OUTER-SPHERE AND INNER-SPHERE PROCESSES IN ORGANIC-CHEMISTRY - REACTION OF TRIFLUOROMETHYL BROMIDE WITH ELECTROCHEMICALLY GENERATED AROMATIC ANION RADICALS AND SULFUR-DIOXIDE ANION RADICALS [J].
ANDRIEUX, CP ;
GELIS, L ;
SAVEANT, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :786-791
[2]   OUTER-SPHERE DISSOCIATIVE ELECTRON-TRANSFER TO ORGANIC-MOLECULES - A SOURCE OF RADICALS OR CARBANIONS - DIRECT AND INDIRECT ELECTROCHEMISTRY OF PERFLUOROALKYL BROMIDES AND IODIDES [J].
ANDRIEUX, CP ;
GELIS, L ;
MEDEBIELLE, M ;
PINSON, J ;
SAVEANT, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) :3509-3520
[3]  
BOIKO VN, 1977, ZH ORG KHIM+, P1057
[4]   FLUORINATED ORGANOMETALLICS - PERFLUOROALKYL AND FUNCTIONALIZED PERFLUOROALKYL ORGANOMETALLIC REAGENTS IN ORGANIC-SYNTHESIS [J].
BURTON, DJ ;
YANG, ZY .
TETRAHEDRON, 1992, 48 (02) :189-275
[5]   CONDENSATION OF PERFLUOROALKYL IODIDES WITH UNSATURATED NITROGEN-COMPOUNDS [J].
CANTACUZENE, D ;
WAKSELMAN, C ;
DORME, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (12) :1365-1371
[6]  
CANTACUZENE D, 1975, Patent No. 2354310
[7]   COLLISIONAL IONIZATION BETWEEN ALKALI ATOMS AND SOME METHANE DERIVATIVES - ELECTRON-AFFINITIES FOR CH3NO2, CF3L, AND CF3BR [J].
COMPTON, RN ;
REINHARDT, PW ;
COOPER, CD .
JOURNAL OF CHEMICAL PHYSICS, 1978, 68 (10) :4360-4367
[8]   SYNTHESIS OF PERFLUOROALKYL CARBOXYLIC-ACIDS BY REACTION OF PERFLUOROALKYL IODIDES WITH ELECTROGENERATED SUPEROXIDE ION [J].
DAPREMONTAVIGNON, C ;
CALAS, P ;
COMMEYRAS, A ;
AMATORE, C .
JOURNAL OF FLUORINE CHEMISTRY, 1991, 51 (03) :357-379
[9]   POLARIZABILITY, BASICITY AND NUCLEOPHILIC CHARACTER [J].
EDWARDS, JO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (09) :1819-1820