3574-58-1

Usage

InChI:InChI=1/C10H18O/c11-10-7-3-1-5-9(10)6-2-4-8-10/h9,11H,1-8H2

Upstream product

• 694-59-7 pyridine N-oxide 
• 493-01-6 cis-decalin 
• 493-02-7 trans-Decalin 
• 87307-15-1 6-bromocyclododecanone 
• 91-17-8 decalin 

Downstream Products

• 51953-08-3 2-(4-bromo-butyl)-cyclohexanone 
• 87307-15-1 6-bromocyclododecanone 
• 64-18-6 formic acid 
• 57289-63-1 (4ar,8ar)-octahydronaphthalene-4a,8a-diol 
• 1126-18-7 2-butylcyclohexanone 

Relevant academic research and scientific papers

Ozonation of decalin as a model saturated cyclic molecule: A spectroscopic study

Ozonolysis is used for oxidation of a model cyclic molecule-decalin, which may be consid-ered as an analog of saturated cyclic molecules present in heavy oil. The conversion of decalin exceeds 50% with the highest yield of formation of acids about 15–17%. Carboxylic acids, ketones/aldehydes, and alcohols are produced as intermediate products. The methods of UV-visible, transmission IR, at-tenuated total reflection IR-spectroscopy, NMR and mass-spectrometry were used to identify reaction products and unravel a possible reaction mechanism. The key stage of the process is undoubtedly the activation of the first C-H bond and the formation of peroxide radicals.

Alkane oxidation catalysed by a self-folded multi-iron complex

A preorganised ligand scaffold is capable of coordinating multiple Fe(II) centres to form an electrophilic CH oxidation catalyst. This catalyst oxidises unactivated hydrocarbons including simple, linear alkanes under mild conditions in good yields with selectivity for the oxidation of secondary CH bonds. Control complexes containing a single metal centre are incapable of oxidising unstrained linear hydrocarbons, indicating that participation of multiple centres aids the CH oxidation of challenging substrates.

Chemoselective hydroxylation of aliphatic sp3 C-H bonds using a ketone catalyst and aqueous H2O2

The first ketone-catalyzed method for the oxidation of aliphatic C-H bonds is reported. The reaction conditions employ aryl trifluoromethyl ketones in catalytic amounts and hydrogen peroxide as the terminal oxidant. Hydroxylation is stereospecific and chemoselective for tertiary over secondary C-H bonds. A catalytic cycle invoking a dioxirane as the active oxidant is proposed.

An iron catalyst for oxidation of alkyl C-H bonds showing enhanced selectivity for methylenic sites

Many are called but few are chosen: A nonheme iron complex catalyzes the oxidation of alkyl C-H bonds by using H2O2 as the oxidant, showing an enhanced selectivity for secondary over tertiary C-H bonds (see scheme). Copyright

Selective activation of secondary C-H bonds by an iron catalyst: Insights into possibilities created by the use of a carboxyl-containing bipyridine ligand

In this work, we report the discovery of a carboxyl-containing iron catalyst 1 (FeII-DCBPY, DCBPY = 2,2′-bipyridine-4,4′- dicarboxylic acid), which could activate the C-H bonds of cycloalkanes with high secondary (2°) C-H bond selectivity. A turnover number (TN) of 11.8 and a 30% yield (based on the H2O2 oxidant) were achieved during the catalytic oxidation of cyclohexane by 1 under irradiation with visible light. For the transformation of cycloalkanes and bicyclic decalins with both 2° and tertiary (3°) C-H bonds, 1 always preferred to oxidise the 2° C-H bonds to the corresponding ketone and alcohol products; the 2°/3° ratio ranged between 78/22 and >99/1 across 7 examples. 18O isotope labelling experiments, ESR experiments, a PPh3 method and the catalase method were used to characterize the reaction process during the oxidation. The success of 1 showed that, in addition to using a bulky catalyst, high 2° C-H bond selectivity could also be achieved using a less bulky molecular iron complex as the catalyst.

Efficient stereo- and regioselective hydroxylation of alkanes catalysed by a bulky polyoxometalate

Direct functionalization of alkanes by oxidation of C-H bonds to form alcohols under mild conditions is a challenge for synthetic chemistry. Most alkanes contain a large number of C-H bonds that present difficulties for selectivity, and the oxidants employed often result in overoxidation. Here we describe a divanadium-substituted phosphotungstate that catalyses the stereo- and regioselective hydroxylation of alkanes with hydrogen peroxide as the sole oxidant. Both cyclic and acyclic alkanes were oxidized to form alcohols with greater than 96% selectivity. The bulky polyoxometalate framework of the catalyst results in an unusual selectivity that can lead to the oxidation of secondary rather than the weaker tertiary C-H bonds. The catalyst also avoids wasteful decomposition of the stoichiometric oxidant, which can result in the production of hydroxyl radicals and lead to non-selective oxidation and overoxidation of the desired products.

The selective functionalization of saturated hydrocarbons. Part 46. An investigation of Udenfriend's system under Gif conditions

Under Gif conditions using ascorbic acid as reductant and oxygen as oxidant in pyridine, the selectivity for secondary hydrogen functionalization is exceptional. EDTA (ethylenediamine-tetra-acetic acid) is not needed as a ligand for iron.

Oxidation with the "O2 - H2O2 - Vauauium complex - Pyrazine-2-carboxylic acid" reagent 9. Oxidation of cyclohexene and decalin

The oxidation of cyclohexene with hydrogen peroxide catalyzed by a vanadium complex and pyrazine-2-carboxylic acid (PCA) in air results in the formation of cyclohex-2-enyl hydroperoxide as the main product and cyclohex-2-enol, cyclohex-2-enone, cyclohex-3-enyl hydroperoxide, cyclohex-3-enol, cyclohexanol, cyclohexane, and 1,2-epoxycyclohexane in lesser amounts. The composition of the products of oxidation of decalin isomers with the system in question is similar to those obtained in the photochemical oxidation with hydrogen peroxide in air and in the oxidation with air in the presence of anthraquinone. A proposed mechanism for the oxidation includes the initiation by hydroxyl radicals generated from hydrogen peroxide under the action of the V - PCA system.

Oxidations by Methyl(trifluoromethyl)dioxirane. 2. Oxyfunctionalization of Saturated Hydrocarbons

The reaction of methyl(trifluoromethyl)dioxirane (1b), a novel dioxirane species, with two open-chain, four cyclic, and five polycyclic saturated hydrocarbons and two aralkyl hydrocarbons in CH2Cl2/1,1,1-trifluoropropanone has been studied; under mild conditions (-22 to 0 deg C), it gives alcohols and/or ketones (deriving from further oxidation of secondary alcohols) in high yields and within very short reaction times.Primary C-H bonds are not appreciably oxidized and high regioselectivities were determined for attack at tertiary over secondary C-H bonds, with theexception of norbornane, which showed opposite regioselectivity.The reaction is also highly stereoselective, since hydroxylations of cis- and trans-decalin and of cis- and trans-1,2-dimethylcyclohexane were found to be in each case stereospecific with retention.From kinetic data, Ea = 14.3 kcal mol-1 and log A = 9.9 were estimated for cyclohexane oxidation.Relative rates change in the order cyclohexane (0.78) octane (9.2) adamantane (146); cis-1,2-dimethylcyclohexane was observed to be 7-fold more reactive than its trans isomer, demonstrating remarkable discrimination for equatorial vs axial C-H attack (also noticed in the case of cis- and trans-decalin).The relative rate of oxidation of cumene vs ethylbenzene was found to be ca. 3.1 (after statistical correction), i.e., in sharp excess over values usually recorded in classical radical H-atom abstraction from benzylic position.Rate constants determined for the reactions of cumene and of ethylbenzene show the title dioxirane (1b) is more reactive than dimethyldioxirane (1a) by factors of ca. 600 and over 700, respectively.The whole of theobservations is better accommodated by an "oxenoid" mechanism, involving concerted O-atom insertion by dioxirane into C-H bonds of hydrocarbons.