RUTHENIUM DIOXIDE IN FLUORO ACID-MEDIUM .5. APPLICATION TO THE NON PHENOLIC OXIDATIVE COUPLING OF DIARYLBUTANES - CONFORMATIONAL STUDIES OF CIS AND TRANS DEOXYSCHIZANDRINS

被引:21
作者
DHAL, R [1 ]
LANDAIS, Y [1 ]
LEBRUN, A [1 ]
LENAIN, V [1 ]
ROBIN, JP [1 ]
机构
[1] UNIV MAINE,INST TECHNOL,DEPT CHIM,F-72017 LE MANS,FRANCE
关键词
RUTHENIUM DIOXIDE; DIARYLBUTANES; DEOXYSCHIZANDRINS; ARYLTETRALINS;
D O I
10.1016/S0040-4020(01)80826-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ruthenium (IV) dioxide dihydrate in fluoro acidic medium was found to be a very efficient agent for the non phenolic oxidative coupling of diarylbutanes. We observed along with the expected aryl-aryl coupling, an unusual aryl-benzyl coupling, leading to a known class of lignans, the aryltetralins. Conformational studies of resultant cis and trans deoxyschizandrins were performed using high resolution NMR and molecular models.
引用
收藏
页码:1153 / 1164
页数:12
相关论文
共 32 条
[1]   SYNTHESIS OF (+/-)-DEOXYSCHIZANDRIN [J].
BIFTU, T ;
HAZRA, BG ;
STEVENSON, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (09) :2276-2281
[2]   X-RAY CRYSTALLOGRAPHIC DETERMINATION OF ABSOLUTE-CONFIGURATIONS AND CONFORMATIONS OF 2 CONFORMATIONAL ISOMERS OF 1,2,3,4-DIBENZO-TRANS-6,7-DIBROMO-1,3-CYCLOOCTADIENE, A 2,2'-BRIDGED BIPHENYL [J].
BORECKA, B ;
CAMERON, TS ;
LINDEN, A ;
RASHIDIRANJBAR, P ;
SANDSTROM, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (03) :1185-1190
[3]   CONSTITUENTS OF EUPOMATIA SPECIES .6. THE STRUCTURES OF EUPODIENONE-1, EUPODIENONE-2 AND EUPODIENONE-3 [J].
BOWDEN, BF ;
READ, RW ;
TAYLOR, WC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (08) :1823-1831
[4]   CONSTITUENTS OF EUPOMATIA SPECIES .7. DIENONE-PHENOL AND DIENOL-BENZENE REARRANGEMENTS IN THE EUPODIENONE-1 SERIES [J].
BOWDEN, BF ;
READ, RW ;
TAYLOR, WC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (04) :799-817
[5]  
BROWN HC, 1976, J ORG CHEM, V41, P3064
[6]   OXIDATIVE COUPLING OF LIGNANS .2. NON-PHENOLIC COUPLING OF DIARYLBUTANE LIGNANS RELATED TO MATAIRESINOL DIMETHYL ETHER [J].
BUCKLETON, JS ;
CAMBIE, RC ;
CLARK, GR ;
CRAW, PA ;
RICKARD, CEF ;
RUTLEDGE, PS ;
WOODGATE, PD .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1988, 41 (03) :305-324
[7]  
BURKET U, 1982, MOL MECHANICS
[8]   OXIDATIVE COUPLING OF LIGNANS .3. NON-PHENOLIC OXIDATIVE COUPLING OF DEOXYPODORHIZON AND RELATED-COMPOUNDS [J].
CAMBIE, RC ;
CRAW, PA ;
RUTLEDGE, PS ;
WOODGATE, PD .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1988, 41 (06) :897-918
[9]   CONSTITUENTS OF EUPOMATIA SPECIES .11. NEW EUPODIENONE LIGNANS FROM THE FLOWERS OF EUPOMATIA-LAURINA [J].
CARROLL, AR ;
TAYLOR, WC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (11) :1871-1879
[10]   STEREOCHEMISTRY OF THE 1,2,3,4-DIBENZ-1,3-CYCLOOCTADIENE SYSTEM [J].
DVORKEN, LV ;
SMYTH, RB ;
MISLOW, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (02) :486-492