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Homologation Of Carboxylic Acids By Improved Methods Based On Radical Chain Chemistry Of Acyl Derivatives Of N-hydroxy-2-thiopyridone

D. H. Barton, Chern Ching-Yuh, J. C. Jászberényi
Published 1992 · Chemistry

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Abstract Reaction of substituted terminal olefins with carbon radicals generated carboxylic acids gives adducts that can be transformed to one carbon atom longer homo-acids in high overall yield. With 6b yields are very good and the conditions of hydrolysis exceptionally mild.
This paper references
10.1016/S0040-4039(00)92696-0
Radical nitrile transfer with methanesulfonyl cyanide or p-toluenesulfonyl cyanide to carbon radicals generated from the acyl derivatives of N-hydroxy-2-thiopyridone
D. H. Barton (1991)
10.1021/CR00097A001
Radical chemistry associated with the thiocarbonyl group
D. Crich (1989)
10.1002/CBER.19821150126
Trimethylsilycyanid als Umpolungsreagens, VIII. Derivate des 2‐(Trimethylsiloxy)‐2‐propennitrils. Synthesen und allgemeine Eigenschaften
U. Hertenstein (1982)
10.1002/CBER.19280610538
Synthesen mit Diazo‐methan, V.: Über die Reaktion der Säurechloride mit Diazo‐methan
F. Arndt (1928)
10.1039/C39830000939
New and improved methods for the radical decarboxylation of acids
D. Barton (1983)
10.1016/S0040-4020(01)97173-X
The invention of new radical chain reactions. Part VIII. Radical chemistry of thiohydroxamic esters; A new method for the generation of carbon radicals from carboxylic acids
D. Barton (1985)
10.1016/S0040-4039(00)92693-5
Homologation of acids via carbon radicals generated from the acyl derivatives of N-hydroxy-2-thiopyridone. (The two-carbon problem).
H. Derek (1991)
10.1016/S0040-4020(01)82012-3
N-hydroxypyridine-2-thione carbamates. IV. A comparison of 5-exo cyclizations of an aminyl radical and an aminium cation radical
M. Newcomb (1990)
10.1016/S0040-4039(00)92615-7
The generation and reactivity of oxygen centered radicals from the photolysis of derivatives of N-hydroxy-2-thiopyridone.
D. H. Barton (1991)
10.1016/0040-4039(88)85103-7
New entry to syn-β-hydroxy-α-amino acids
Mosahiro Hirama (1988)
10.1016/S0040-4020(01)86853-8
Radical reactions in organic synthesis
M. Ramaiah (1987)
10.1021/JA00183A035
Kinetics of the reversible .beta.-scission of the cyclopentyloxy radical
A. J. Beckwith (1989)
10.1016/S0040-4039(01)84596-2
Radical addition to vinyl sulphones and vinyl phosphonium salts
D. H. Barton (1985)
10.1016/S0040-4020(01)85980-9
The invention of radical reactions part XVIII. A convenient solution to the 1-carbon problem (R-CO2H → R-13CO2H)
D. H. Barton (1988)
10.1016/S0040-4039(00)88851-6
N-hydroxypyridine-2-thione carbamates. VII, Intermolecular addition and addition-cyclization reactions of aminium cation radicals
M. Newcomb (1990)
10.1002/ANIE.198400691
The Scope of Radical CC‐Coupling by the “Tin Method”
B. Giese (1984)
10.1016/S0040-4039(00)71214-7
Cyclizations and intermolecular additions of alkoxycarbonyloxy radicals from N-hydroxypyridine-2-thione carbonates
M. Newcomb (1991)
10.1021/JO00939A026
Ferric chloride in acetic anhydide. Mild and versatile reagent for the cleavage of ethers
B. Ganem (1974)
10.1016/S0040-4039(01)80910-2
Facile generation of dialkylaminyl radicals from n-hydroxypyridine-2-thione carbamates. Application in kinetic studies of small ring cycloalkylaminyl radical ring openings
M. Newcomb (1985)
10.1016/S0040-4020(01)82013-5
N-hydroxypyridine-2-thione carbamates. v. syntheses of alkaloid skeletons by aminium cation radical cyclizations
M. Newcomb (1990)
10.1002/ANIE.198307531
Formation of CC Bonds by Addition of Free Radicals to Alkenes
B. Giese (1983)
10.1002/CBER.190904202126
Über Phenyl-sulfoxyessigsäure
R. Pummerer (1909)
10.1002/CBER.19831160923
Phenyleffekte bei radikalischen Additionen an Alkene
B. Giese (1983)
10.1016/S0040-4039(00)71215-9
DIASTEREOSELECTIVE FORMATION OF CYCLIC CARBONATES BY CYCLIZATION OF ALKENYLOXYCARBONYLOXY RADICALS
A. J. Beckwith (1991)
10.1016/S0040-4039(00)94229-1
Radical chemistry of thiohydroxamic acid esters
D. Barton (1983)
10.1002/CBER.19280610864
Nachträge zu den „Synthesen mit Diazo‐methan”︁
F. Arndt (1928)
10.1021/JA00244A060
N-Hydroxypyridine-2-thione carbamates as aminyl and aminium radical precursors. Cyclizations for synthesis of the pyrrolidine nucleus
M. Newcomb (1987)
10.1021/JA00221A051
Generation of alkoxy radicals from N-alkoxypyridinethiones
A. J. Beckwith (1988)
10.1016/S0040-4020(01)82014-7
N-Hyroxypyridine-2-thione carbamates. VI. Functionalization of carbon radicals formed by aminium cation radical cyclizattons
M. Newcomb (1990)
10.1039/P19860000039
The invention of new radical chain reactions. Part 9. Further radical chemistry of thiohydroxamic esters; formation of carbon–carbon bonds
D. Barton (1986)
10.1002/CBER.19270600616
Diazo‐methan und o‐Nitroverbindungen, II.: N‐Oxy‐isatin aus o‐Nitro‐benzoylchlorid
F. Arndt (1927)
10.1002/CBER.19861190228
Trimethylsilylcyanid als Umpolungsreagens. IX: Enolester von Acylcyaniden: Synthesen und allgemeine Eigenschaften
U. Hertenstein (1986)
10.1002/ANIE.198109652
CC Bond Formation Between “Electron‐Rich” and “Electron‐Deficient” Alkenes
B. Giese (1981)
10.1016/S0040-4039(01)80099-X
Formation of carbon-carbon bonds with radicals derived from the esters of thiohydroxamic acids
D. Barton (1984)
10.1016/S0040-4039(00)97193-4
N-hydroxy-2-pyridinethione: A mild and convenient source of hydroxyl radicals
J. Boivin (1990)
10.1002/CBER.19100430241
Über Phenylsulfoxy-essigsäure. (II.)
R. Pummerer (1910)
10.1016/S0040-4039(01)99826-0
A practical alternative to the hunsdiecker reaction
D. Barton (1983)



This paper is referenced by
10.1016/S0040-4020(01)81288-6
Radical decarboxylative alkylation of tartaric acid
D. H. Barton (1993)
10.1002/CHIN.200418284
The Photochemistry of Barton Esters
P. Dalko (2004)
10.1016/0040-4020(94)01054-4
The invention of radical reactions. Part XXXIV. Homologation of carboxylic acids to α-keto carboxylic acids by Barton-ester based radical chain chemistry☆
D. H. Barton (1995)
10.1016/0040-4020(94)01099-L
A facile preparation method for α,α-difluoroalkanecarboxylic acids and esters. A formal difluoromethylene insertion to alkanecarboxylic acids using radical reaction
T. Okano (1995)
10.1016/j.tet.2019.130883
Two-way homologation of aliphatic aldehydes: Both one-carbon shortening and lengthening via the same intermediate
J. W. Yoo (2020)
10.1016/0040-4039(93)88090-6
Chain-elongation and degradation of carboxylic acids by barton-ester based radical chemistry
D. H. Barton (1993)
10.1039/A802507J
Relative β-elimination rates of heteroatoms from alkyl and aminyl radicals
S. Kim (1998)
10.1016/J.TETLET.2004.04.180
Novel route to carboxylic acids via the DCME reaction
J. A. Soderquist (2004)
10.1016/S0040-4039(00)78245-1
Synthesis and application of chlorodithiocarbonates, thionothiocarbonates, and thionoselenocarbonates in radical chain reactions
D. H. Barton (1994)
10.1016/S0040-4039(00)60171-5
Synthesis of substituted malonic acids from carbon radicals generated from carboxylic acids
D. H. Barton (1992)
10.1002/CHIN.199302148
Homologation of Carboxylic Acids by Improved Methods Based on Radical Chain Chemistry of Acyl Derivatives of N-Hydroxy-2-thiopyridone.
D. Barton (1993)
10.1021/ja505964r
Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin
L. Chu (2014)
10.1002/anie.201609662
Nickel-Catalyzed Barton Decarboxylation and Giese Reactions: A Practical Take on Classic Transforms.
Tian Qin (2017)
10.1016/S0040-4039(00)79284-7
Oxidation of phenylhydrazones of α-keto esters with hypervalent organoiodine reagents
D. H. Barton (1993)
10.1080/00397919608003550
Radical Chemistry Based on (+)-cis-Pinononic and (+)-CIS-Pinonic Acids
D. H. Barton (1996)
10.1021/OL0002370
BtCH(2)TMS-assisted homologation of carboxylic acids: A safe alternative to the arndt-eistert reaction
M. Katritzky (2000)
10.1002/9781118662083.COT09-004
Formation of Nitriles, Carboxylic Acids, and Derivatives by Carbonyl Homologation and Degradation
R. Larock (2018)
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