OXIDATION OF CIS-PINANE AND TRANS-PINANE WITH RUO4 GENERATED IN-SITU

被引:25
作者
COUDRET, JL [1 ]
WAEGEL, B [1 ]
机构
[1] FAC SCI & TECH ST JEROME,LASCO,CNRS,URA 1409,STEREOCHIM LAB,CASE 532,F-13397 MARSEILLE 20,FRANCE
关键词
RUTHENIUM COMPLEXES; OXO COMPLEXES; OXIDATION; HYDROXYLATION; ALKANES; CARBON CARBON BOND CLEAVAGE; BRIDGEHEAD REACTIVITY;
D O I
10.1016/0020-1693(94)03900-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The products obtained by oxidation of cis- and trans-pinane (1a and 1b) by RuO4 generated in situ have been analyzed. Examination of their structure shows that two mechanisms are operating: a concerted mechanism postulated by ourselves and a more energetic mechanism considered by Bakke, which involves the development of a partial positive charge on the carbon to be oxidized.
引用
收藏
页码:115 / 122
页数:8
相关论文
共 34 条
[1]  
BAKKE JE, COMMUNICATION
[2]   DERIVATIZATION OF SATURATED-HYDROCARBONS - THE MECHANISM OF RUO4 OXIDATIONS [J].
BAKKE, JM ;
BRAENDEN, JE .
ACTA CHEMICA SCANDINAVICA, 1991, 45 (04) :418-423
[3]   THE RUO4 OXIDATION OF CYCLIC SATURATED-HYDROCARBONS - FORMATION OF ALCOHOLS [J].
BAKKE, JM ;
LUNDQUIST, M .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1986, 40 (06) :430-433
[4]   THE MECHANISM OF RUO4-MEDIATED OXIDATIONS OF SATURATED-HYDROCARBONS - SOLVENT EFFECTS AND SUBSTITUENT EFFECTS [J].
BAKKE, JM ;
FROHAUG, AE .
ACTA CHEMICA SCANDINAVICA, 1994, 48 (02) :160-164
[5]   THE MECHANISM OF RUO4-MEDIATED OXIDATIONS OF SATURATED-HYDROCARBONS - REACTIVITY, KINETIC ISOTOPE EFFECT AND ACTIVATION PARAMETERS [J].
BAKKE, JM ;
BETHELL, D .
ACTA CHEMICA SCANDINAVICA, 1992, 46 (07) :644-649
[6]  
BARETTA AJ, 1970, B SOC CHIM FR, P3985
[7]  
BERSON JA, 1964, MOL REARRANGEMENTS, P111
[8]   UBER EIN ACYLAL DES DIMETHYLKETENS [J].
BESTIAN, H ;
GUNTHER, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1963, 75 (18) :841-&
[9]   RUTHENIUM CATALYZED OXIDATION OF ALKANES [J].
CARLSEN, PHJ .
SYNTHETIC COMMUNICATIONS, 1987, 17 (01) :19-23
[10]   A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS [J].
CARLSEN, PHJ ;
KATSUKI, T ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) :3936-3938