Catalytic Osmium Tetroxide Oxidation of Olefins:<i>cis</i>‐1,2‐Cyclohexanediol

VanRheenen, V.; Y., D.; Hartley, William M.

doi:10.1002/0471264180.os058.08

Cited by 31 publications

(46 citation statements)

References 19 publications

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“…Amine N-oxides can be prepared from amines with 30% aqueous hydrogen peroxide in a noncatalytic slow reaction [97,110]. At elevated temperatures this oxidation proceeds at a reasonable rate and has been used in industrial applications.…”

Section: Stoichiometric Reactionsmentioning

confidence: 99%

Selective Oxidation of Amines and Sulfides

Bäckvall

2010

Modern Oxidation Methods

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A large number of methods are known in the literature for the oxidation of sulfides (thioethers) to sulfoxides by electrophilic reagents. These include the use of peracids [10], NaIO 4 , hypochlorites, MnO 2 , CrO 3 , SeO 2 , and iodosobenzene. The use of these reagents has been reviewed up to 2005 [3, 4]. Hydrogen peroxide can also be used as a direct oxidant, although this reaction is slow in the absence of catalyst. Its use in catalytic reactions is discussed below in Section 8.2.2. 7 5 9 9 5 Ph S 8 15 94 280j 8 Selective Oxidation of Amines and Sulfides

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Section: Stoichiometric Reactionsmentioning

confidence: 99%

Selective Oxidation of Amines and Sulfides

Bäckvall

2010

Modern Oxidation Methods

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“…Surprisingly, neither the dihydroxylation of this compound nor that of any related benzoquinone diacetals has yet been described in the literature, so we first tested various reagents and sets of conditions for cis-selective dihydroxylation of olefins. KMnO 4 [25] or I 2 /wet AgOAc [26] gave the dihydroxylated product in very poor yield or not at all, respectively, but better results were obtained with the OsO 4 /NMO [27] or RuCl 3 /NaIO 4 [28] reagents. Under carefully optimized conditions (Scheme 4), syn-diol 6 could be obtained in 64 % yield.…”

Section: Dihydroxylation Of Benzoquinone Bis(ethylene Acetal)mentioning

confidence: 99%

Synthesis of Both Enantiomers of Conduritol C Tetraacetate and of meso‐Conduritol D Tetraacetate by Oxidation of Benzoquinone Bis(ethylene acetal)

Lang

Ziegler

2007

Eur J Org Chem

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Epoxidation of p‐benzoquinone bis(ethylene acetal) (1) with m‐chloroperbenzoic acid or hydrogen peroxide/benzonitrile afforded corresponding monoepoxide 2, which was converted into p‐benzoquinone mono(ethylene acetal) monoepoxide 5 with perchloric acid. Dihydroxylation of 1 with osmium tetroxide or ruthenium trichloride/sodium periodate afforded corresponding cis‐diol 6, which was subsequently acetylated to give diacetate 7. One ethyleneacetal moiety in 7 could be selectively hydrolyzed with silica gel/ferric chloride under solvent‐free conditions to give ketone 8, which, upon reduction with sodium borohydride and subsequent acetylation of the formed alcohol group, afforded two diastereomeric triacetates 10. Hydrolysis of the remaining acetal functions in the two diastereomers 10, followed by reduction of the second carbonyl group as described above, afforded racemic conduritol C and meso‐conduritol D tetraacetates 12 and 13, respectively. Enzymatic resolution of the racemic arabino‐configured triacetate 10 with Lipozym failed, while the ribo‐configured counterpart reacted smoothly to give enantiomerically pure D‐ribo‐ and L‐ribo‐configured triacetates 10. The latter pair of enantiomerically pure triacetates were converted into both enantiomers of conduritol C tetraacetate 13 as described for the racemic compounds. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…3, 4 They often used as potential cytoximes for 25 the treatment of solid tumors and also as ligands for the preparation of useful transition metal complexes. 5,6 As a catalyst, especially in epoxidation reactions, amine N-oxides displayed a wide range of advantages in chemical industries.…”

Section: Introductionmentioning

confidence: 99%

Catalytic N-oxidation of tertiary amines on RuO2NPs anchored graphene nanoplatelets

Gopiraman¹,

Bang²,

Babu³

et al. 2014

Catal. Sci. Technol.

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Ultrafine ruthenium oxide nanoparticles (RuO 2 NPs) of an average diameter of 1.3 nm were anchored on graphene nanoplatelets (GNPs) using Ru(acac) 3 precursor by a very simple dry synthesis method. The resultant material (GNPs-RuO 2 NPs) was used as a heterogeneous catalyst for the N-oxidation of tertiary amines for the first time. The transmission electron microscopic (TEM) images of the GNPs-RuO 2 NPs 10 showed an excellent attachment of RuO 2 NPs on GNPs. The loading of Ru in GNPs-RuO 2 NPs was 2.68 wt%, as confirmed by scanning electron microscope-energy dispersive spectroscopy (SEM-EDS). X-ray photoelectron spectrum (XPS) and X-ray diffraction pattern (XRD) of GNPs-RuO 2 NPs revealed that the chemical state of Ru on GNPs was +4. After the optimization of reaction conditions for N-oxidation of triethylamine, the scope of the reaction was extended with a various aliphatic, alicyclic and aromatic 15 tertiary amines. The GNPs-RuO 2 NPs showed an excellent catalytic activity in terms of yields even at a very low amount of Ru catalyst (0.13 mol%). The GNPs-RuO 2 NPs was heterogeneous in nature, chemically as well as physically very stable and reused for up to 5 times.

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Catalytic Osmium Tetroxide Oxidation of Olefins:cis‐1,2‐Cyclohexanediol

Abstract: Catalytic osmium tetroxide oxidation of olefins: cis ‐1,2‐cyclohexanediol product: cis‐1,2‐ Cyclohexanediol (2) intermediate: N ‐Methylmorpholine N ‐oxide (1) can also be purchased from Eastman Organic Chemicals or Fluka A G

Cited by 31 publications

References 19 publications

Selective Oxidation of Amines and Sulfides

Selective Oxidation of Amines and Sulfides

Synthesis of Both Enantiomers of Conduritol C Tetraacetate and of meso‐Conduritol D Tetraacetate by Oxidation of Benzoquinone Bis(ethylene acetal)

Catalytic N-oxidation of tertiary amines on RuO2NPs anchored graphene nanoplatelets

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