MINIMIZING GEOMETRIC ISOMERIZATION DURING OXIDATION OF ALLYLIC ALCOHOLS TO ALDEHYDES

被引：31

作者：

XIAO, XY ^{[1
]}

PRESTWICH, GD ^{[1
]}

机构：

[1] SUNY STONY BROOK,DEPT CHEM,STONY BROOK,NY 11794

来源：

SYNTHETIC COMMUNICATIONS | 1990年 / 20卷 / 20期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1080/00397919008051535

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidation of allylic alcohols with MnO2/Na2CO3 gives from 20:1 to 99:1 selectivity for the geometrically retained enals, whereas MnO2 alone gives 10% or more of the isomerized enals. © 1990, Taylor & Francis Group, LLC. All rights reserved.

引用

页码：3125 / 3130

页数：6

共 7 条

[1]

ALLINGER NL, 1972, ORGANIC CHEM, P509

[2] MU-OXO-BIS(CHLOROTRIPHENYLBISMUTH) - MILD REAGENT FOR THE OXIDATION OF THE HYDROXY GROUP, ESPECIALLY IN ALLYLIC ALCOHOLS [J].

BARTON, DHR ;

KITCHIN, JP ;

MOTHERWELL, WB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (24) :1099-1100

[3] NEW METHODS FOR OXIDATION OF ALDEHYDES TO CARBOXYLIC ACIDS AND ESTERS [J].

COREY, EJ ;

GILMAN, NW ;

GANEM, BE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5616-&

[4] SUBSTITUTION AND REARRANGEMENT REACTIONS OF ALLYLIC COMPOUNDS [J].

DEWOLFE, RH ;

YOUNG, WG .

CHEMICAL REVIEWS, 1956, 56 (04) :753-901

[5]

FATIADI AJ, 1976, SYNTHESIS-STUTTGART, P65

[6]

MATSUMOTO M, 1984, J ORG CHEM, V49, P3436

[7] BIS-TETRABUTYLAMMONIUM DICHROMATE AS A NEUTRAL AND SELECTIVE OXIDANT OF HYDROXY COMPOUNDS [J].

SANTANIELLO, E ;

FERRABOSCHI, P .

SYNTHETIC COMMUNICATIONS, 1980, 10 (01) :75-81

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