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 38 条

[11] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS
BARTON, DHR
MCCOMBIE, SW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16): : 1574 - 1585
[12] IMPROVED METHODS FOR THE RADICAL DEOXYGENATION OF SECONDARY ALCOHOLS
BARTON, DHR
JASZBERENYI, JC
[J]. TETRAHEDRON LETTERS, 1989, 30 (20) : 2619 - 2622
[13] RADICAL DEOXYGENATION OF TERTIARY ALCOHOLS
BARTON, DHR
HARTWIG, W
MOTHERWELL, RSH
MOTHERWELL, WB
STANGE, A
[J]. TETRAHEDRON LETTERS, 1982, 23 (19) : 2019 - 2022
[14] OLEFIN SYNTHESIS BY RADICAL METHODS FROM XANTHATE, SELENOBENZOATE AND THIONOCARBONATE DERIVATIVES OF BETA-HYDROXY SULFONES
BARTON, DHR
JASZBERENYI, JC
TACHDJIAN, C
[J]. TETRAHEDRON LETTERS, 1991, 32 (24) : 2703 - 2706
[15] THE INVENTION OF RADICAL REACTIONS .19. THE SYNTHESIS OF VERY HINDERED QUINONES
BARTON, DHR
SAS, W
[J]. TETRAHEDRON, 1990, 46 (10) : 3419 - 3430
[16] CHATGILIALOGLU C, 1990, SYNLETT, P219
[17] TRIS(TRIMETHYLSILYL)SILANE - A NEW REDUCING AGENT
CHATGILIALOGLU, C
GRILLER, D
LESAGE, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) : 3641 - 3642
[18] RADICAL CHAIN REDUCTION OF ALKYL-HALIDES, DIALKYL SULFIDES AND O-ALKYL S-METHYL DITHIOCARBONATES TO ALKANES BY TRIALKYLSILANES
COLE, SJ
KIRWAN, JN
ROBERTS, BP
WILLIS, CR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01): : 103 - 112
[19] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1.
CURRAN, DP
[J]. SYNTHESIS-STUTTGART, 1988, (06): : 417 - 439
[20] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .2.
CURRAN, DP
[J]. SYNTHESIS-STUTTGART, 1988, (07): : 489 - 513

← 1 2 3 4 →