Preparation and structures of crystalline aromatic cation-radical salts. Triethyloxonium hexachloroantimonate as a novel (one-electron) oxidant

被引:133
作者
Rathore, R [1 ]
Kumar, AS [1 ]
Lindeman, SV [1 ]
Kochi, JK [1 ]
机构
[1] Univ Houston, Dept Chem, Houston, TX 77204 USA
关键词
D O I
10.1021/jo980407a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Triethyloxonium hexachloroantimonate [Et3O+SbCl6-] is a selective oxidant of aromatic donors (ArH), and it allows the facile preparation and isolation of crystalline paramagnetic salts [ArH+., SbCl6-] for the X-ray structure determination of various aromatic cation radicals. The mechanistic relationship between the Meerwein salt [Et3O+SbCl6-] and the pure Lewis acid oxidant SbCl5 is based on a prior ethyl transfer from oxygen to chlorine within the ion pair.
引用
收藏
页码:5847 / 5856
页数:10
相关论文
共 77 条
[1]   RADICAL CATIONS - GENERATION BY PHOTOCHEMICAL ELECTRON-TRANSFER AND FRAGMENTATION [J].
ALBINI, A ;
FASANI, E ;
DALESSANDRO, N .
COORDINATION CHEMISTRY REVIEWS, 1993, 125 (1-2) :269-281
[2]   OXIDATION OF AROMATIC-COMPOUNDS BY DIAZONIUM IONS - UNEXPECTEDLY FACILE ELECTRON-TRANSFER REACTIONS [J].
ANDERSEN, ML ;
HANDOO, KL ;
PARKER, VD .
ACTA CHEMICA SCANDINAVICA, 1991, 45 (09) :983-985
[3]  
[Anonymous], 1986, ORGANIC SYNTHESIS OX
[4]   ABSORPTION SPECTRA OF DIMER CATIONS .3. NAPHTHALENE AND ANTHRACENE DERIVATIVES AND PYRENE [J].
BADGER, B ;
BROCKLEH.B .
TRANSACTIONS OF THE FARADAY SOCIETY, 1969, 65 (562P) :2588-&
[5]   ABSORPTION SPECTRA OF DIMER CATIONS .2. BENZENE DERIVATIVES [J].
BADGER, B ;
BROCKLEH.B .
TRANSACTIONS OF THE FARADAY SOCIETY, 1969, 65 (562P) :2582-&
[6]   ION RADICALS .37. PREPARATION AND ISOLATION OF CATION RADICAL TETRAFLUOROBORATES BY USE OF NITROSONIUM TETRAFLUOROBORATE [J].
BANDLISH, BK ;
SHINE, HJ .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (03) :561-563
[7]  
Bard A. J., 1976, ADV PHYSICAL ORGANIC, V13, P155
[8]   CATION RADICAL PERICYCLIC-REACTIONS [J].
BAULD, NL ;
BELLVILLE, DJ ;
HARIRCHIAN, B ;
LORENZ, KT ;
PABON, RA ;
REYNOLDS, DW ;
WIRTH, DD ;
CHIOU, HS ;
MARSH, BK .
ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (10) :371-378
[9]  
BAUMGARTEN M, 1994, TOP CURR CHEM, V169, P1
[10]   CONTRIBUTIONS OF PULSE-RADIOLYSIS TO CHEMISTRY [J].
BAXENDALE, JH ;
RODGERS, MAJ .
CHEMICAL SOCIETY REVIEWS, 1978, 7 (02) :235-263