One-Pot Oxidative Cleavage of Olefins to Synthesize Carboxylic Acids by a Telescoped Ozonolysis-Oxidation Process

被引：19

作者：

Cochran, Brian M. ^{[1
]}

机构：

[1] Amgen Inc, Synthet Technol, Proc Dev, Thousand Oaks, CA 91320 USA

来源：

SYNLETT | 2016年 / 27卷 / 02期

关键词：

ozonolysis; carboxylic acids; green chemistry; alkenes; oxidation; CONVERSION; ALKENES; HYDROVINYLATION; ALDEHYDES; MECHANISM; AMINES;

D O I：

10.1055/s-0035-1560659

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild one-pot ozonolysis-oxidation process of alkenes to synthesize carboxylic acids is described. Conducting the ozonolysis in an aqueous organic solvent eliminates secondary ozonide formation and the intermediates generated are readily converted into a carboxylic acid by adding sodium chlorite. Following a reductive quench, the desired acids are isolated in high purity and high yield by simple extraction.

引用

页码：245 / 248

页数：4

共 30 条

[1] The Development of Continuous Process for Alkene Ozonolysis Based on Combined in Situ FTIR, Calorimetry, and Computational Chemistry [J].

Allian, Ayman D. ;

Richter, Steve M. ;

Kallemeyn, Jeffrey M. ;

Robbins, Timothy A. ;

Kishore, Vimal .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2011, 15 (01) :91-97

[2]

Bailey P.S., 1978, Ozonation in Organic Chemistry: Olefinic Compounds, V1

[3] EIN KRISTALLISIERTES PRIMAROZONID .11. [J].

CRIEGEE, R ;

SCHRODER, G .

CHEMISCHE BERICHTE-RECUEIL, 1960, 93 (03) :689-700

[4] MECHANISM OF OZONOLYSIS [J].

CRIEGEE, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (11) :745-752

[5] SELECTIVE OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS WITH SODIUM-CHLORITE HYDROGEN-PEROXIDE [J].

DALCANALE, E ;

MONTANARI, F .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :567-569

[6]

Geletneky C, 1998, EUR J ORG CHEM, V1998, P1625

[7] 3,4-Dihydropyrimido(1,2-a)indol-10(2H)-ones as potent non-peptidic inhibitors of caspase-3 [J].

Havran, Lisa M. ;

Chong, Dan C. ;

Childers, Wayne E. ;

Dollings, Paul J. ;

Dietrich, Arlene ;

Harrison, Boyd L. ;

Marathias, Vasilios ;

Tawa, Gregory ;

Aulabaugh, Ann ;

Cowling, Rebecca ;

Kapoor, Bhupesh ;

Xu, Weixin ;

Mosyak, Lidia ;

Moy, Franklin ;

Hum, Wah-Tung ;

Wood, Andrew ;

Robichaud, Albert J. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (22) :7755-7768

[8] THE MECHANISTIC STUDY AND SYNTHETIC APPLICATIONS OF THE BASE TREATMENT IN THE OZONOLYTIC REACTIONS [J].

HON, YS ;

LIN, SW ;

LU, L ;

CHEN, YJ .

TETRAHEDRON, 1995, 51 (17) :5019-5034

[9] An Ozonolysis-Reduction Sequence for the Synthesis of Pharmaceutical Intermediates in Microstructured Devices [J].

Huebner, Sandra ;

Bentrup, Ursula ;

Budde, Uwe ;

Lovis, Kai ;

Dietrich, Thomas ;

Freitag, Andreas ;

Kuepper, Lukas ;

Jaehnisch, Klaus .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (05) :952-960

[10] Continuous Flow Ozonolysis in a Laboratory Scale Reactor [J].

Irfan, Muhammad ;

Glasnov, Toma N. ;

Kappe, C. Oliver .

ORGANIC LETTERS, 2011, 13 (05) :984-987

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