THE ISOINVERSION PRINCIPLE FOR THE ASYMMETRIC TAUTOMERIZATION OF PHOTODIENOLS

被引：33
作者：
MUZART, J
HENIN, F
PETE, JP
MBOUNGOUMPASSI, A
机构：
[1] Unité Réarrangements Thermiques et Photochimiques Associée au C.N.R.S., Université de Reims Champagne-Ardenne
来源：
TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 12期
关键词：
D O I：
10.1016/S0957-4166(00)82233-8
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
From the study of the tautomerization of prochiral dienols photogenerated in an organic solvent between -76 and +30 degrees C in the presence of optically active aminoalcohols and in using the methodology developed by Scharf's group, the isoinversion temperature of the asymmetric process has been estimated to be -55 degrees C.
引用
收藏
页码：2531 / 2534
页数：4
相关论文
共 31 条
[1]   THE ISOINVERSION PRINCIPLE - A GENERAL-MODEL OF CHEMICAL SELECTIVITY [J].
BUSCHMANN, H ;
SCHARF, HD ;
HOFFMANN, N ;
ESSER, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (05) :477-515
[2]   GENERATION OF SIMPLE ENOLS IN SOLUTION [J].
CAPON, B ;
GUO, BZ ;
KWOK, FC ;
SIDDHANTA, AK ;
ZUCCO, C .
ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (04) :135-140
[3]  
CAPON B, 1989, CHEM FUNCTIONAL GROU, P1063
[4]   PKA AND KETO-ENOL EQUILIBRIUM-CONSTANT OF ACETONE IN AQUEOUS-SOLUTION [J].
CHIANG, Y ;
KRESGE, AJ ;
TANG, YS ;
WIRZ, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (02) :460-462
[5]   ENOLS AND OTHER REACTIVE SPECIES [J].
CHIANG, Y ;
KRESGE, AJ .
SCIENCE, 1991, 253 (5018) :395-400
[6]   DIRECT OBSERVATION OF A PHOTOCHEMICALLY PRODUCED DIENOL - EVIDENCE FOR A NONCATALYZED REKETONIZATION PATHWAY UNAVAILABLE TO SIMPLE ENOLS [J].
DUHAIME, RM ;
WEEDON, AC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (23) :6723-6724
[7]   THE ISOSELECTIVE RELATIONSHIP [J].
GIESE, B .
ACCOUNTS OF CHEMICAL RESEARCH, 1984, 17 (12) :438-442
[8]   BASIS AND LIMITATIONS OF REACTIVITY-SELECTIVITY PRINCIPLE [J].
GIESE, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (03) :125-136
[9]   STUDIES OF HYDROGEN BONDING .3. INTERMOLECULAR HYDROGEN BOND ASSOCIATION BETWEEN NITROGEN COMPOUNDS AND METHANOL, PHENOL, ALPHA-NAPTHTHOL AND PENTACHLOROPHENOL [J].
GRAMSTAD, T .
ACTA CHEMICA SCANDINAVICA, 1962, 16 (04) :807-&
[10]   SIMPLE ENOLS [J].
HART, H .
CHEMICAL REVIEWS, 1979, 79 (06) :515-528
1234