An aqueous silica gel disperse electrolysis system.: N-Oxyl-mediated electrooxidation of alcohols

被引:68
作者
Tanaka, H [1 ]
Kawakami, Y [1 ]
Goto, K [1 ]
Kuroboshi, M [1 ]
机构
[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan
关键词
electrochemistry; oxidation; alcohols; enantioselective;
D O I
10.1016/S0040-4039(00)01979-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Oxyl-mediated electrooxidation of alcohols was performed in an aqueous silica gel disperse system. The newly devised electrolysis system offers an organic solvent-free and operationally simple procedure for oxidation of alcohols and could be successfully applied to kinetic resolution of sec-alcohol as well as enantioselective oxidation of meso-1,4-diol affording optically active gamma -lactone. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:445 / 448
页数:4
相关论文
共 12 条
[1]   INDIRECT ELECTROOXIDATION OF ALCOHOLS BY A DOUBLE MEDIATORY SYSTEM WITH 2 REDOX COUPLES OF [R2N(+)=O]/R2NO. AND [BR. OR BR+]/BR- IN AN ORGANIC AQUEOUS 2-PHASE SOLUTION [J].
INOKUCHI, T ;
MATSUMOTO, S ;
TORII, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2416-2421
[2]   A SELECTIVE AND EFFICIENT METHOD FOR ALCOHOL OXIDATIONS MEDIATED BY N-OXOAMMONIUM SALTS IN COMBINATION WITH SODIUM BROMITE [J].
INOKUCHI, T ;
MATSUMOTO, S ;
NISHIYAMA, T ;
TORII, S .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :462-466
[3]   OXIDATIONS OF DIHYDROXYALKANOATES TO VICINAL TRICARBONYL COMPOUNDS WITH A 4-BZOTEMPO-SODIUM BROMITE SYSTEM OR BY INDIRECT ELECTROLYSIS USING 4-BZOTEMPO AND BROMIDE ION [J].
INOKUCHI, T ;
LIU, P ;
TORII, S .
CHEMISTRY LETTERS, 1994, (08) :1411-1414
[4]   Diastereoselective preparation of a trans, trans 2,3-dimethylchroman-4-ol skeleton: A model synthetic approach to anti-HIV-1 active Calophyllum coumarins [J].
Ishikawa, T ;
Oku, Y ;
Kotake, K .
TETRAHEDRON, 1997, 53 (44) :14915-14928
[5]   Enantioselective electrocatalytic oxidation of racemic sec-alcohols using a chiral 1-azaspiro[5.5]undecane-N-oxyl radical [J].
Kashiwagi, Y ;
Kurashima, F ;
Kikuchi, C ;
Anzai, J ;
Osa, T ;
Bobbitt, JM .
TETRAHEDRON LETTERS, 1999, 40 (35) :6469-6472
[6]  
KASHIWAGI Y, 1996, J CHEM SOC CHEM COMM, P2745
[7]   Electro-oxidative kinetic resolution of sec-alcohols by using an optically active N-oxyl mediator [J].
Kuroboshi, M ;
Yoshihisa, H ;
Cortona, MN ;
Kawakami, Y ;
Gao, Z ;
Tanaka, H .
TETRAHEDRON LETTERS, 2000, 41 (42) :8131-8135
[8]   OXOAMMONIUM SALTS .5. A NEW SYNTHESIS OF HINDERED PIPERIDINES LEADING TO UNSYMMETRICAL TEMPO-TYPE NITROXIDES - SYNTHESIS AND ENANTIOSELECTIVE OXIDATIONS WITH CHIRAL NITROXIDES AND CHIRAL OXOAMMONIUM SALTS [J].
MA, ZK ;
HUANG, QT ;
BOBBITT, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4837-4843
[9]   Enantioselective oxidation of secondary alcohols using a chiral nitroxyl (N-oxoammonium salt) catalyst [J].
Rychnovsky, SD ;
McLernon, TL ;
Rajapakse, H .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) :1194-1195
[10]   NITROXYL-MEDIATED ELECTROOXIDATION OF ALCOHOLS TO ALDEHYDES AND KETONES [J].
SEMMELHACK, MF ;
CHOU, CS ;
CORTES, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (13) :4492-4494