Practical dihydroxylation and C–C cleavage of unsaturated fatty acids

Oakley, Michael A.; Woodward, Simon; Coupland, Keith; Parker, David; Temple-Heald, Clare

doi:10.1016/s1381-1169(99)00213-7

Cited by 46 publications

(35 citation statements)

References 7 publications

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“…Used oxidants such as peracids are regarded as problematic in terms of ecology. An alternative was found by Woodward and co-workers [91] who combined the tungstate-catalyzed synthesis of DSA using the environmentally benign hydrogen peroxide with its aerobic cleavage. They developed a sophisticated two-step one-pot procedure which enables the combination of the systems for dihydroxylation (H 2 WO 4 /H 2 O 2 ) and cleavage of the formed diol (H 2 WO 4 / Co(acac) 3 /N-hydroxyphthalimide/O 2 ).…”

Section: Two-step Catalytic Cleavage Of Oa or Momentioning

confidence: 99%

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Köckritz

Martin

2010

Euro J Lipid Sci & Tech

114

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Section: Two-step Catalytic Cleavage Of Oa or Momentioning

confidence: 99%

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Köckritz

Martin

2010

Euro J Lipid Sci & Tech

114

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“…Woodward and coworkers have applied the NHPI-catalyzed oxidation to the carbon-carbon bond cleavage of diols to carboxylic acids (Equation 29). [96] Unlike 1,2-diols, internal vic-diols such as 2,3-octanediol were selectively oxidized to diketones such as 2,3-octanedione rather than cleaved to carboxylic acids. The conversion of vic-diols to diketones is usually performed by oxidation with metal oxidants such as AgCO 3 [97] and permanganate, [98] and by a TEMPONaOCl system under electrochemical conditions [99] or by a catalytic method using heteropolyoxometalates and H 2 O 2 .…”

Section: Oxidation Of Diolsmentioning

confidence: 99%

Innovation of Hydrocarbon Oxidation with Molecular Oxygen and Related Reactions

2001

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An innovation of the aerobic oxidation of hydrocarbons through catalytic carbon radical generation under mild conditions was achieved by using N‐hydroxyphthalimide (NHPI) as a key compound. Alkanes were successfully oxidized with O2 or air to valuable oxygen‐containing compounds such as alcohols, ketones, and dicarboxylic acids by the combined catalytic system of NHPI and a transition metal such as Co or Mn. The NHPI‐catalyzed oxidation of alkylbenzenes with dioxygen could be performed even under normal temperature and pressure of dioxygen. Xylenes and methylpyridines were also converted into phthalic acids and pyridinecarboxylic acids, respectively, in good yields. The present oxidation method was extended to the selective transformations of alcohols to carbonyl compounds and of alkynes to ynones. The epoxidation of alkenes using hydroperoxides or H2O2 generated in situ from hydrocarbons or alcohols and O 2 under the influence of the NHPI was demonstrated and seems to be a useful strategy for industrial applications. The NHPI method is applicable to a wide variety of organic syntheses via carbon radical intermediates. The catalytic carboxylation of alkanes was accomplished by the use of CO and O2 in the presence of NHPI. In addition, the reactions of alkanes with NO2 and SO2 catalyzed by NHPI provided efficient methods for the synthesis of nitroalkanes and sulfonic acids, respectively. A catalytic carbon‐carbon bond forming reaction was achieved by allowing carbon radicals generated in situ from alkanes or alcohols to react with alkenes under mild conditions. 1 Introduction 2 Discovery of NHPI as Carbon Radical Producing Catalyst from Alkanes 2.1 Historical Background 2.2 Catalysis of NHPI in Aerobic Oxidation 3 NHPI‐Catalyzed Aerobic Oxidation 3.1 Oxidation of Benzylic Compounds 3.2 Alkane Oxidations with Molecular Oxygen 3.3 Oxidation of Alkylbenzenes 3.4 Practical Oxidation of Methylpyridines 3.5 Preparation of Acetylenic Ketones via Alkyne Oxidation 3.6 Oxidation of Alcohols 3.7 Selective Oxidation of Sulfides to Sulfoxides 3.8 Production of Hydrogen Peroxide by Aerobic Oxidation of Alcohols 3.9 Epoxidation of Alkenes using Molecular Oxygen as Terminal Oxidant 4 Carboxylation of Alkanes with CO and O2 5 Utilization of NOx in Organic Synthesis 5.1 First Catalytic Nitration of Alkanes using NO2 5.2 Reaction of NO with Organic Compounds 6 Sulfoxidation of Alkanes Catalyzed by Vanadium 7 Carbon‐Carbon Bond Forming Reaction via Catalytic Carbon Radicals Generated from Various Organic Compounds Assisted by NHPI 7.1 Oxyalkylation of Alkenes with Alkanes and Dioxygen 7.2 Synthesis of α‐Hydroxy‐γ‐lactones by Addition of α‐Hydroxy Carbon Radicals to Unsaturated Esters 7.3 Hydroxyacylation of Alkenes using 1,3‐Dioxolanes and Dioxygen 8 Conclusions

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“…In many cases, their successful application as renewable raw materials in organic synthesis depends on the efficiency of oxidative transformation of their alkyl chain. However, the traditional oxidation with organic hydroperoxides [1][2][3][4][5] is complicated by such serious problems as multistage and complex engineering, considerable consumption of raw materials, risk of explosion, etc. In contrast, the oxidation in biphasic systems in the presence of peroxopolyoxometalate (PPOM) catalysts combined with phase-transfer catalysts such as quaternary ammonium cations, has been proved to be a promising advanced synthesis method [6][7][8][9] 3 ?…”

Section: Introductionmentioning

confidence: 99%

Catalytic oxidation of fatty acids. II. Epoxidation and oxidative cleavage of unsaturated fatty acid esters containing additional functional groups

Khlebnikova

Pai

Fedoseeva

et al. 2009

React Kinet Catal Lett

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Methyl esters of monounsaturated fatty acids were oxidized with aqueous hydrogen peroxide in biphasic organic-aqueous systems in the presence of catalyst [Me(n-C 8 H 17 ) 3 N] 3 {PO 4 [WO(O 2 ) 2 ] 4 }. Epoxidation and oxidative cleavage of the C=C bond were found to proceed with high conversion and selectivity in the absence of organic solvents and under rather mild conditions (T \ 100°C, 1 atm).

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Practical dihydroxylation and C–C cleavage of unsaturated fatty acids

Cited by 46 publications

References 7 publications

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Innovation of Hydrocarbon Oxidation with Molecular Oxygen and Related Reactions

Catalytic oxidation of fatty acids. II. Epoxidation and oxidative cleavage of unsaturated fatty acid esters containing additional functional groups

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