Heterogeneous Permanganate Oxidations. 7. The Oxidation of Aliphatic Side Chains

Noureldin, Nazih A.; Zhao, Dan; Lee, Donald G.

doi:10.1021/jo971168e

Cited by 67 publications

(23 citation statements)

References 17 publications

(24 reference statements)

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“…The products are identical to those obtained under heterogeneous conditions where the reductant is dissolved in an inert solvent; 19 however, the reaction times are reduced from a few days to a few hours at room temperature. Addition of alumina to the solid support decreased the yields of these reactions.…”

Section: Methodssupporting

confidence: 52%

Solvent free permanganate oxidations

Shaabani

Lee

2001

Tetrahedron Letters

147

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Abstract-The oxidations of organic compounds by permanganate under solvent free conditions have been studied. Thiols and primary aromatic amines undergo oxidative coupling reactions to give disulfides and diazenes, respectively, sulfides are oxidized to sulfones, primary and secondary alcohols are converted to aldehydes and ketones, 1,4-diols and cyclic ethers give lactones and arenes are oxidized to the corresponding a-ketones. The experimental procedure is simple and the products are easily isolated in good yields.

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Section: Methodssupporting

confidence: 52%

Solvent free permanganate oxidations

Shaabani

Lee

2001

Tetrahedron Letters

147

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“…[77] Reaction between 3,4-Dihydro-1H-isochromene (34) and HNO 3 in CH 2 Cl 2 : A solution of 3,4-dihydro-1H-isochromene (34, 3.35 g, 25.0 mmol) in CH 2 Cl 2 (5.0 mL) was treated as described in the general oxidation procedure (Ͼ 99% conv. after 1 h), affording 3,4-dihydro-1H-isochromen-1-one (35) [78] in 81% (3.00 g) isolated yield.…”

Section: General Procedures For the Oxidation Of Benzylic Alcohols Andmentioning

confidence: 99%

Oxidation of Benzylic Alcohols and Ethers to Carbonyl Derivatives by Nitric Acid in Dichloromethane

Strazzolini

Runcio

2003

Eur J Org Chem

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Nitric acid in dichloromethane may be successfully employed for the oxidation of benzylic alcohols and ethers to the corresponding carbonyl compounds. The proposed method proved to be of general applicability, affording very good yields of aldehydes and ketones and showing interesting chemoselectivity in many instances, allowing competitive aromatic nitration to be avoided, as well as − in the case of aldehydes − any further oxidation to carboxylic acids. The reaction probably proceeds by a radical mechanism, the active species in the oxidation process being NO2. Competitive formation of nitro esters was observed in some cases, whereas poor results were obtained with allylic and non‐benzylic substrates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…Racemic HHCB (0.3 g 0.12 mmol) was dissolved in 20 ml dichloromethane and a finely powdered mixture of potassium permanganate (1.5 g) and copper sulfate pentahydrate (1.5 g) dissolved in 20 ml dichloromethane added. The whole was stirred under reflux for 72 h. 26 The product was filtered through a celite pad, the residue washed with dichloromethane (3 × 20 ml) and diethyl ether (3 × 10 ml) and the combined organic phases dried over sodium sulfate. …”

Section: 1233-pentamethylindanmentioning

confidence: 99%