CONFORMATIONAL EFFECTS IN THE HYDROLYSES OF RIGID BENZYLIC EPOXIDES - IMPLICATIONS FOR DIOL EPOXIDES OF POLYCYCLIC-HYDROCARBONS

被引:82
作者
SAYER, JM
YAGI, H
SILVERTON, JV
FRIEDMAN, SL
WHALEN, DL
JERINA, DM
机构
[1] NIADDKD,BIOORGAN CHEM LAB,BETHESDA,MD 20205
[2] NHLBI,CHEM LAB,BETHESDA,MD 20205
[3] UNIV MARYLAND,DEPT CHEM,CHEM DYNAM LAB,CATONSVILLE,MD 21228
关键词
D O I
10.1021/ja00371a029
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:1972 / 1978
页数:7
相关论文
共 35 条
[1]   RING INVERSION IN CYCLOHEXENE [J].
ANET, FAL ;
HAQ, MZ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (14) :3147-&
[2]   REACTIONS OF 2-ARYLCYCLOHEXANONES .3. CYANOETHYLATIONS AND MANNICH REACTIONS [J].
BACHMANN, WE ;
WICK, LB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (08) :3388-3392
[3]   METHOD FOR THE CLEAVAGE OF OSMATE ESTERS [J].
BARAN, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (02) :257-257
[4]   CONFIGURATIONAL AND CONFORMATIONAL STEREOSELECTIVITY IN THE ACID-CATALYZED RING-OPENING OF 1-PHENYLCYCLOHEXENE OXIDES [J].
BATTISTINI, C ;
CROTTI, P ;
DAMIANI, D ;
MACCHIA, F .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) :1643-1647
[5]   EFFECT OF SUBSTITUENTS ON STEREOSELECTIVITY OF ACID-CATALYZED HYDROLYSIS OF A SERIES OF ARYLOXIRANS - NEW APPLICATION OF HAMMETT EQUATION [J].
BATTISTINI, C ;
BALSAMO, A ;
BERTI, G ;
CROTTI, P ;
MACCHIA, B ;
MACCHIA, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (17) :712-713
[6]   SOLUTION CHEMISTRY OF THE SYN-TETRAHYDRODIOL AND ANTI-TETRAHYDRODIOL EPOXIDES, THE SYN-TETRAHYDRODIMETHOXY AND ANTI-TETRAHYDRODIMETHOXY EPOXIDES, AND THE 1,2-TETRAHYDRO EPOXIDES AND 1,4-TETRAHYDRO EPOXIDES OF NAPHTHALENE [J].
BECKER, AR ;
JANUSZ, JM ;
BRUICE, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (19) :5679-5687
[7]  
BUCOURT R, 1974, TOP STEREOCHEM, V8, P159
[8]   MOLECULAR REARRANGEMENTS .14. THE HYDROGEN DEUTERIUM ISOTOPE EFFECT IN THE PINACOL REARRANGEMENT OF TRIARYLETHYLENE GLYCOLS [J].
COLLINS, CJ ;
RAINEY, WT ;
SMITH, WB ;
KAYE, IA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (02) :460-465
[9]   Stereochemistry of as-octahydrophenanthrene [J].
Cook, JW ;
Hewett, CL ;
Robinson, AM .
JOURNAL OF THE CHEMICAL SOCIETY, 1939, :168-177
[10]   PRELIMINARY SYNTHESES IN THE MORPHINE SERIES .3. MICHAEL CONDENSATIONS WITH 2-ARYLCYCLOHEX-2-ENONES AND CYCLISATION OF THE PRODUCTS TO OCTAHYDROPHENANTHRENE DERIVATIVES [J].
GINSBURG, D ;
PAPPO, R .
JOURNAL OF THE CHEMICAL SOCIETY, 1951, (APR) :938-945