A STEREOSELECTIVE REDUCTION OF DIBENZO-18-CROWN-6 ETHER TO DICYCLOHEXYL-18-CROWN-6 ETHER

被引:20
作者
LANDRE, PD
LEMAIRE, M
RICHARD, D
GALLEZOT, P
机构
[1] UNIV LYON 1,ESCIL,CATALYSE & SYNTH ORGAN LAB,BAT 308,43 BD DU 11 NOVEMBRE 1918,F-69622 VILLEURBANNE,FRANCE
[2] CNRS,INST RECH CATALYSE,F-69626 VILLEURBANNE,FRANCE
来源
JOURNAL OF MOLECULAR CATALYSIS | 1993年 / 78卷 / 03期
关键词
D O I
10.1016/0304-5102(93)87055-D
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Dibenzo-18-crown-6 ether is reduced to dicyclohexano-18-crown-6 ether under very mild conditions (room temperature and atmospheric hydrogen pressure) in the presence of rhodium salt and phase-transfer reagents. Control over the stereoselectivity of the reduction can be achieved through the proper choice of the phase-transfer agent. Moreover, at higher pressure, the stereoselectivity can be increased up to a 95/5 ratio of the syn/anti isomers of the dicyclohexano-18-crown-6 ether.
引用
收藏
页码:257 / 261
页数:5
相关论文
共 9 条
[1]   HYDROGENATION OF ARENES BY THE RHCL3-ALIQUAT 336 CATALYST .3. SELECTIVE REDUCTION OF POLYCYCLIC COMPOUNDS [J].
AMER, I ;
AMER, H ;
ASCHER, R ;
BLUM, J ;
SASSON, Y ;
VOLLHARDT, KPC .
JOURNAL OF MOLECULAR CATALYSIS, 1987, 39 (02) :185-194
[2]   HYDROGENATION OF ARENES BY THE RHCL3-ALIQUAT-336 CATALYST .2. REDUCTION OF NAPHTHALENE DERIVATIVES TO TETRALINS [J].
AMER, I ;
AMER, H ;
BLUM, J .
JOURNAL OF MOLECULAR CATALYSIS, 1986, 34 (02) :221-228
[3]   HYDROGENATION OF ARENES BY THE RHCL3-ALIQUAT-336 CATALYST .4. HYDROGEN-DEUTERIUM EXCHANGE AND OTHER MECHANISTIC FEATURES [J].
BLUM, J ;
AMER, I ;
VOLLHARDT, KPC ;
SCHWARZ, H ;
HOHNE, G .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2804-2813
[4]   CATALYTIC-HYDROGENATION OF OLEFINS, ACETYLENES AND ARENES BY RHODIUM TRICHLORIDE AND ALIQUAT-336 UNDER PHASE-TRANSFER CONDITIONS [J].
BLUM, J ;
AMER, I ;
ZORAN, A ;
SASSON, Y .
TETRAHEDRON LETTERS, 1983, 24 (38) :4139-4142
[5]   STEREOCHEMISTRY OF NONCOVALENT INTERACTIONS IN ORGANIC AND METAL CATIONIC COMPLEXES [J].
COXON, AC ;
LAIDLER, DA ;
PETTMAN, RB ;
STODDART, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (26) :8260-8262
[6]   CALORIMETRIC TITRATION STUDY OF INTERACTION OF SEVERAL UNIVALENT AND BIVALENT-CATIONS WITH 15-CROWN-5, 18-CROWN-6, AND 2 ISOMERS OF DICYCLOHEXO-18-CROWN-6 IN AQUEOUS-SOLUTION AT 25 DEGREESC AND MU=0.1 [J].
IZATT, RM ;
TERRY, RE ;
HAYMORE, BL ;
HANSEN, LD ;
DALLEY, NK ;
AVONDET, AG ;
CHRISTENSEN, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (24) :7620-7626
[7]   EXCEEDINGLY MILD, SELECTIVE AND STEREOSPECIFIC PHASE-TRANSFER-CATALYZED HYDROGENATION OF ARENES [J].
JANUSZKIEWICZ, KR ;
ALPER, H .
ORGANOMETALLICS, 1983, 2 (08) :1055-1057
[8]   DICYCLOHEXANO-18-CROWN-6 ETHER - A NEW SELECTIVE EXTRACTANT FOR NUCLEAR-FUEL REPROCESSING [J].
LEMAIRE, M ;
GUY, A ;
CHOMEL, R ;
FOOS, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (17) :1152-1154
[9]  
Pedersen C.J., 1972, ORG SYNTH, V52, P66