1724-39-6Relevant articles and documents
Comparative study of the reactions of n-BuMgBr and n-BuLi with cyclododecanone
Zakharkin, L. I.,Churilova, I. M.,Petrovskii, P. V.
, p. 863 - 865 (1993)
The composition of the products obtained in the reaction of n-BuMgBr and n-BuLi with cyclododecanone (1) has revealed that 1 exhibits the properties of a sterically hindered ketone.The highest yield of 1-butylcyclododecanol (2) was achieved with the use of n-BuMgBr, but in this case cyclododecanol was also formed, whereas the use of n-BuLi led to the tertiary alcohol more distinctly.Dehydration of alcohol 2 resulted in a mixture of three olefins containing up to 90percent of E- and Z- isomers of 1-butylcyclododecene.
SELECTIVE OXIDATION OF SATURATED HYDROCARBONS USING AN ELECTROCHEMICAL MODIFICATION OF THE GIF SYSTEM.
Balavoine, Gilbert,Barton, Derek H. R.,Boivin, Jean,Gref, Aurore,Ozbalik, Nubar,Riviere, Henriette
, p. 2849 - 2852 (1986)
The Gif system for selective hydrocarbon oxidation can be carried out replacing the zinc by a cathodic electrochemical reduction; the yields obtained and the selectivities observed are very similar.
Synergistic oxidation of cyclohexane and hydrogen sulfide under Gif conditions
Barton, Derek H. R.,Li, Tingsheng,MacKinnon, John
, p. 557 - 558 (1997)
Saturated hydrocarbons and hydrogen sulfide can be synergistically oxidised by oxygen (or air) to give efficiently ketones (and the corresponding alcohols) and sulfur in the presence of a Gif catalyst based on FeII, picolinic acid and 4-tert-butylpyridine with acetonitrile as solvent at room temperature and nearly neutral pH.
The functionalization of saturated hydrocarbons. Part XIX. Oxidation of alkanes by H2O2 in pyridine catalyzed by copper(II) complexes. A Gif-type reaction
Barton,Csuhai,Doller,Geletii
, p. 6561 - 6570 (1991)
The Cu(II)-catalyzed oxidation of saturated hydrocarbons by hydrogen peroxide proceeds in pyridine-acetic acid solutions affording mainly ketones as the reaction product. The conversion of hydrocarbon is about 20-30%. This system (called GoChAgg) shares with the Fe(III)-catalyzed system (GoAgg(II)) its unusual chemical characteristics.
Catalytic hydrogenation of aldehydes and ketones using cinchona–bipyridyl-based palladium catalyst
Chidambaram, Ramasamy R.,Sadhasivam, Velu,Mariyappan, Mathappan,Siva, Ayyanar
, p. 373 - 384 (2019)
Understanding the need for simple, robust and low effluents, in chemical processes, we have developed an elegant protocol for the catalytic reduction of aldehydes and ketones to corresponding alcohols which are used in synthetic fragrance applications using cinchona alkaloid-derived palladium catalyst. This system holds good for very low catalyst loading surfaces with the formation of fewer impurities and negligible decomposition under moderate pressure. The conversions and yields range from moderate to good (60–80%).
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Wasserman,H.H. et al.
, p. 1863 - 1866 (1976)
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Horinaka,A. et al.
, p. 2095 - 2098 (1975)
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Kobayashi
, p. 5093 (1972)
Efficient oxidation of cycloalkanes with simultaneously increased conversion and selectivity using O2 catalyzed by metalloporphyrins and boosted by Zn(AcO)2: A practical strategy to inhibit the formation of aliphatic diacids
Shen, Hai-Min,Wang, Xiong,Ning, Lei,Guo, A-Bing,Deng, Jin-Hui,She, Yuan-Bin
, (2020/11/20)
The direct sources of aliphatic acids in cycloalkanes oxidation were investigated, and a strategy to suppress the formation of aliphatic acids was adopted through enhancing the catalytic transformation of oxidation intermediates cycloalkyl hydroperoxides to cycloalkanols by Zn(II) and delaying the emergence of cycloalkanones. Benefitted from the delayed formation of cycloalkanones and suppressed non-selective thermal decomposition of cycloalkyl hydroperoxides, the conversion of cycloalkanes and selectivity towards cycloalkanols and cycloalkanones were increased simultaneously with satisfying tolerance to both of metalloporphyrins and substrates. For cyclohexane, the selectivity towards KA-oil was increased from 80.1% to 96.9% meanwhile the conversion was increased from 3.83 % to 6.53 %, a very competitive conversion level with higher selectivity compared with current industrial process. This protocol is not only a valuable strategy to overcome the problems of low conversion and low selectivity lying in front of current cyclohexane oxidation in industry, but also an important reference to other alkanes oxidation.
Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes
Bhunia, Anup,Bergander, Klaus,Daniliuc, Constantin Gabriel,Studer, Armido
supporting information, p. 8313 - 8320 (2021/03/08)
Hydration of alkenes using first row transition metals (Fe, Co, Mn) under oxygen atmosphere (Mukaiyama-type hydration) is highly practical for alkene functionalization in complex synthesis. Different hydration protocols have been developed, however, control of the stereoselectivity remains a challenge. Herein, highly diastereoselective Fe-catalyzed anaerobic Markovnikov-selective hydration of alkenes using nitroarenes as oxygenation reagents is reported. The nitro moiety is not well explored in radical chemistry and nitroarenes are known to suppress free radical processes. Our findings show the potential of cheap nitroarenes as oxygen donors in radical transformations. Secondary and tertiary alcohols were prepared with excellent Markovnikov-selectivity. The method features large functional group tolerance and is also applicable for late-stage chemical functionalization. The anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.
