16214-27-0Relevant articles and documents
A novel method for protection and deprotection of the carbonyl groups in 1,2-indanedione by conversion to dioxa-dithiapropellanes
Almog, Joseph,Zehavy, Yirmi,Cohen, Shmuel
, p. 3285 - 3288 (2003)
1,2-Indanedione reacts with two equivalents of 2-mercaptoethanol to produce, instead of the expected 1,2-bis(1,3-oxathiolane), a dioxa-dithia[4.4.3] propellane. Other 1,2-indanediones produce analogous compounds. The protecting groups are removed at room temperature with NBS in aqueous acetone, to produce the original diketone.
Electron Spin Resonance Studied of Substituents effects. 5. Combined Effects of Orbital Symmetry and Substituents on the Methylene Hyperfine Splitting in 1,2-Indansemidiones
Strom, E. Thomas
, p. 5686 - 5689 (1995)
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Tris(pentafluorophenyl)borane-Catalyzed Oxygen Insertion Reaction of α-Diazoesters (α-Diazoamides) with Dimethyl Sulfoxide
Wu, Xiao-Yang,Gao, Wen-Xia,Zhou, Yun-Bing,Liu, Miao-Chang,Wu, Hua-Yue
supporting information, p. 750 - 754 (2022/01/19)
A tris(pentafluorophenyl)borane-catalyzed oxidation reaction of α-diazoesters (α-diazo amides) with dimethyl sulfoxide has been developed. The reaction proceeds under metal free conditions to afford a series α-ketoesters and α-ketoamides. The synthetic utility of this protocol is demonstrated through synthetic transformations and scaled-up synthesis. (Figure presented.).
A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones
Ma, Zhiming,Ren, Peng,Song, Tao,Xiao, Jianliang,Yang, Yong,Yuan, Youzhu
, p. 4617 - 4629 (2020/05/19)
We herein report the fabrication of a bifunctional iron nanocomposite catalyst, in which two catalytically active sites of Fe-Nx and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under mild reaction conditions. Furthermore, it could be easily recovered for successive recycling without appreciable loss of activity. Mechanistic studies disclose that the direct oxidation of alkenes proceeds via the formation of an epoxide as intermediate followed by either acid-catalyzed Meinwald rearrangement to give ketones with one carbon shorter or nucleophilic ring-opening to generate 1,2-diketones in a cascade manner. This study not only opens up a fancy pathway in the rational design of Fe-N-C catalysts but also offers a simple and efficient method for accessing industrially important ketones and 1,2-diketones from alkenes in a cost-effective and environmentally benign fashion.
Emulation of racemase activity by employing a pair of stereocomplementary biocatalysts
Gruber, Christian C.,Nestl, Bettina M.,Gross, Johannes,Hildebrandt, Petra,Bornscheuer, Uwe T.,Faber, Kurt,Kroutil, Wolfgang
, p. 8271 - 8276 (2008/04/01)
Racemization is the key step to turn a kinetic resolution process into dynamic resolution. A general strategy for racemization under mild reaction conditions by employing stereoselective biocatalysts is presented, in which racemization is achieved by employing a pair of stereocomplementary biocatalysts that reversibly interconvert an sp3 to a sp2 center. The formal interconversion of the enantiomers proceeds via a prochiral sp 2 intermediate the formation of which is catalyzed either by two stereocomplementary enzymes or by a single enzyme with low stereoselectivity. By choosing appropriate reaction conditions, the amount of the prochiral intermediate is kept to a minimum. This general strategy, which is applicable to redox enzymes (e.g., by acting on R2CHOH and R2CHNHR groups) and lyase-catalyzed addition-elimination reactions, was proven for the racemization of secondary alcohols by employing alcohol dehydrogenases. Thus, enantiopure chiral alcohols were used as model substrates and were racemized either with highly stereoselective biocatalysts or by using (rarely found) non-selective enzymes.