MECHANISM OF THE MITSUNOBU ESTERIFICATION REACTION .1. THE INVOLVEMENT OF PHOSPHORANES AND OXYPHOSPHONIUM SALTS

被引:107
作者
CAMP, D [1 ]
JENKINS, ID [1 ]
机构
[1] GRIFFITH UNIV,SCH SCI,NATHAN,QLD 4111,AUSTRALIA
关键词
D O I
10.1021/jo00274a016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:3045 / 3049
页数:5
相关论文
共 22 条
[1]  
Ball D H, 1969, Adv Carbohydr Chem Biochem, V24, P139
[2]   MECHANISM OF THE TRIPHENYLPHOSPHINE AND DIETHYL AZODICARBOXYLATE INDUCED DEHYDRATION REACTIONS (MITSUNOBU REACTION) - THE CENTRAL ROLE OF PENTAVALENT PHOSPHORUS INTERMEDIATES [J].
GROCHOWSKI, E ;
HILTON, BD ;
KUPPER, RJ ;
MICHEJDA, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (24) :6876-6877
[3]   FORMATION OF 3',6'-ANHYDROSUCROSE BY MITSUNOBU DEHYDRATION OF SUCROSE [J].
GUTHRIE, RD ;
JENKINS, ID ;
THANG, S ;
YAMASAKI, R .
CARBOHYDRATE RESEARCH, 1988, 176 (02) :306-308
[4]   DERIVATIVES OF SUCROSE 3',4'-EPOXIDE [J].
GUTHRIE, RD ;
JENKINS, ID ;
THANG, S ;
YAMASAKI, R .
CARBOHYDRATE RESEARCH, 1983, 121 (SEP) :109-117
[5]   THE MECHANISM OF THE MITSUNOBU REACTION - A P-31 NMR-STUDY [J].
GUTHRIE, RD ;
JENKINS, ID .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (04) :767-774
[6]   A MECHANISTIC STUDY OF THE MITSUNOBU ESTERIFICATION REACTION [J].
HUGHES, DL ;
REAMER, RA ;
BERGAN, JJ ;
GRABOWSKI, EJJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (19) :6487-6491
[7]   IMPROVED SYNTHESIS OF CORD FACTOR ANALOGS VIA THE MITSUNOBU REACTION [J].
JENKINS, ID ;
GOREN, MB .
CHEMISTRY AND PHYSICS OF LIPIDS, 1986, 41 (3-4) :225-235
[8]   INTERMEDIATE FROM TRIPHENYLPHOSPHINE-TETRACHLOROMETHANE-ALCOHOL REACTION - RELATIVE RATES OF INTERMEDIATE FORMATION, KINETICS, AND MECHANISM OF INTERMEDIATE DECOMPOSITION [J].
JONES, LA ;
SUMNER, CE ;
FRANZUS, B ;
HUANG, TTS ;
SNYDER, EI .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2821-2827
[9]  
KELLY JW, 1986, J ORG CHEM, V51, P5492
[10]  
KOSOLAPOFF GM, 1972, ORGANIC PHOSPHORUS C, V3