THE INVENTION OF RADICAL REACTIONS .21. SIMPLE METHODS FOR THE RADICAL DEOXYGENATION OF PRIMARY ALCOHOLS

被引：57

作者：

BARTON, DHR ^{[1
]}

BLUNDELL, P ^{[1
]}

DORCHAK, J ^{[1
]}

JANG, DO ^{[1
]}

JASZBERENYI, JC ^{[1
]}

机构：

[1] TEXAS A&M UNIV SYST,DEPT CHEM,COLLEGE STN,TX 77843

来源：

TETRAHEDRON | 1991年 / 47卷 / 43期

关键词：

THIONOCARBONATES; TRIBUTYLTIN HYDRIDE; TRIPHENYLSILANE; DIPHENYLSILANE; PHENYLSILANE; RADICAL DEOXYGENATIONS;

D O I：

10.1016/S0040-4020(01)86502-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel radical-chain deoxygenations of primary alcohols are described. The alcohols are acylated with the reagents pentafluorophenyl chlorothionoformate, 2,4,6-trichlorophenyl chlorothionoformate and 4-fluorophenyl chlorothionoformate and the intermediate thionocarbonates are deoxygenated with tributyltin hydride, triphenylsilane, diphenylsilane or phenylsilane in high-yielding reactions.

引用

页码：8969 / 8984

页数：16

共 50 条

[41] The invention of radical reactions .37. A convenient radical synthesis of dialkyl diselenides from carboxylic acids.
Barton, DHR
Fontana, G
TETRAHEDRON, 1996, 52 (34) : 11163 - 11176
[42] REACTIONS OF THIANTHRENE CATION-RADICAL WITH ACYCLIC AND CYCLIC ALCOHOLS
SHINE, HJ
YUEH, W
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13): : 3553 - 3559
[43] Catalytic Radical-Polar Crossover Reactions of Allylic Alcohols
Touney, Eric E.
Foy, Nicholas J.
Pronin, Sergey V.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (49) : 16982 - 16987
[44] THE INVENTION OF RADICAL REACTIONS .18. DECARBOXYLATIVE RADICAL-ADDITION TO ARSENIC, ANTIMONY, AND BISMUTH PHENYLSULFIDES - A NOVEL SYNTHESIS OF NOR-ALCOHOLS FROM CARBOXYLIC-ACIDS
BARTON, DHR
BRIDON, D
ZARD, SZ
TETRAHEDRON, 1989, 45 (09) : 2615 - 2626
[45] Unexpected C-arylation of a gibberellin: A cautionary note on the radical deoxygenation of homoallylic secondary alcohols
Mander, LN
Sherburn, MS
TETRAHEDRON LETTERS, 1996, 37 (24) : 4255 - 4258
[46] STUDIES IN CI MASS-SPECTROMETRY .21. RADICAL REACTIONS WITH SELECTED ORGANIC-COMPOUNDS IN THE GAS-PHASE
BUDZIKIEWICZ, H
DRABNER, G
ORGANIC MASS SPECTROMETRY, 1989, 24 (08): : 535 - 538
[47] Radical fluorination reactions by thermal and photoinduced methods
Lantano, Beatriz
Postigo, Al
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (47) : 9954 - 9973
[48] A SIMPLE-MODEL FOR FREE-RADICAL REACTIONS
KLESSINGER, M
HOWELER, U
CROATICA CHEMICA ACTA, 1986, 59 (03) : 653 - 658
[49] FREE-RADICAL REACTIONS WITH SIMPLE BIOCHEMICAL SYSTEMS
REDPATH, JL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1980, 180 (AUG): : 27 - CHED
[50] INFLUENCE OF TEMPERATURE ON STERIC FACTORS IN SIMPLE AND RADICAL REACTIONS
STEPUKHOVICH, AD
DOKLADY AKADEMII NAUK SSSR, 1956, 107 (03): : 436 - 439

← 1 2 3 4 5 →