66003-63-2Relevant articles and documents
CATALYTIC CARBOXYLATION OF ACTIVATED ALKANES AND/OR OLEFINS
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Page/Page column 64; 65, (2018/02/28)
The present invention relates to a method of reacting starting materials with an activating group, namely alkanes carrying a leaving group and/or olefins, with carbon dioxide under transition metal catalysis to give carboxyl group-containing products. It is a special feature of the method of the present invention that the carboxylation predominantly takes place at a preferred position of the molecule irrespective of the position of the activating group. The carboxylation position is either an aliphatic terminus of the molecule or it is a carbon atom adjacent to a carbon carrying an electron withdrawing group. The course of the reaction can be controlled by appropriately choosing the reaction conditions to yield the desired regioisomer.
Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide
Juliá-Hernández, Francisco,Moragas, Toni,Cornella, Josep,Martin, Ruben
, p. 84 - 88 (2017/05/12)
Catalytic carbon-carbon bond formation has enabled the streamlining of synthetic routes when assembling complex molecules. It is particularly important when incorporating saturated hydrocarbons, which are common motifs in petrochemicals and biologically relevant molecules. However, cross-coupling methods that involve alkyl electrophiles result in catalytic bond formation only at specific and previously functionalized sites. Here we describe a catalytic method that is capable of promoting carboxylation reactions at remote and unfunctionalized aliphatic sites with carbon dioxide at atmospheric pressure. The reaction occurs via selective migration of the catalyst along the hydrocarbon side-chain with excellent regio- and chemoselectivity, representing a remarkable reactivity relay when compared with classical cross-coupling reactions. Our results demonstrate that site-selectivity can be switched and controlled, enabling the functionalization of less-reactive positions in the presence of a priori more reactive ones. Furthermore, we show that raw materials obtained in bulk from petroleum processing, such as alkanes and unrefined mixtures of olefins, can be used as substrates. This offers an opportunity to integrate a catalytic platform en route to valuable fatty acids by transforming petroleum-derived feedstocks directly.
Site-Selective Catalytic Carboxylation of Unsaturated Hydrocarbons with CO2 and Water
Gaydou, Morgane,Moragas, Toni,Juliá-Hernández, Francisco,Martin, Ruben
supporting information, p. 12161 - 12164 (2017/09/12)
A catalytic protocol that reliably predicts and controls the site-selective incorporation of CO2 to a wide range of unsaturated hydrocarbons utilizing water as formal hydride source is described. This platform unlocks an opportunity to catalytically repurpose three abundant, orthogonal feedstocks under mild conditions.
Functionalised nanoparticles, their production and use
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Page/Page column 13, (2014/09/03)
Stable complexes are described, formed by mono- and di-functional compounds bound to nanoparticles composed of various types of transition metal oxides and of metals useful in the production processes of different types of new materials (such as for examp
FUNCTIONALISED NANOPARTICLES, THEIR PRODUCTION AND USE
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Page/Page column 11, (2012/07/27)
Stable complexes are described, formed by mono- and di-functional compounds bound to nanoparticles composed of various types of transition metal oxides and of metals useful in the production processes of different types of new materials (such as for examp
Synthesis of new, pyrene-containing, metal-chelating lipids and sensing of cupric ions
Roy, Bidhan C.,Chandra, Binita,Hromas, Daniel,Mallik, Sanku
, p. 11 - 14 (2007/10/03)
(Matrix presented) The syntheses of several saturated, pyrene-containing, metal-chelating lipids are described. These lipids are capable of strongly binding to transition metal ions employing the metal-chelating headgroup. The excimer-to-monomer ratio of
Chain-Substituted Lipids in Monolayer Films. A Study of Molecular Packing
Menger, F. M.,Wood, M. G.,Richardson, S.,Zhou, Q.,Elrington, A. R.,Sherrod, M. J.
, p. 6797 - 6803 (2007/10/02)
A series of highly purified fatty acids and phospholipids, each possessing a chain substituent of varying size (methyl, n-butyl, or phenyl) at varying locations (carbon 4, 8, 12, or 16 of an 18-carbon chain) were synthesized.Pressure-area isotherms, obtained with the aid of a film balance, revealed how these molecules, either individually or admixed, pack in monomolecular films.Two examples will illustrate here the type of information secured by the method. (a) The presence of a methyl at carbon 16 of a single phospholipid chain has a negligible effect on the molecular packing within a "liquid" film.A methyl on carbon 16 of both chains, on the other hand, is highly expansive.Even a single methyl at position 8 perturbs the film packing appreciably, thus indicating less available space near the center of the chain. (b) Deviation from ideality in mixed fatty acid films can be explained by interdigitation that reduces steric repulsion among the substituents.It is also possible to observe by means of film balance techniques the extrusion of 8-butylstearic acid when it contaminates a film composed largely of stearic acid.Approximate SHADOW calculations could, in many cases, provide film areas in reasonable agreement with experiment.
A NEW METHOD FOR THE PRODUCTION OF 15-HYDROXYPENTADECANOIC ACID
Andreev, V. M.,Polyakova, S. G.,Bazhulina, V. I.,Khrustova, Z. S.,Smirnova, V. V.,etc.
, p. 79 - 83 (2007/10/02)
15-Hydroxypentadecanoic acid was synthesized by electrochemical condensation of monoethyl 1,10-decanedicarboxylate with 5-acetoxyvaleric acid at a platinum anode.The acetoxyvaleric acid was obtained in two ways, i.e., by acetolysis of 5-chlorovaleric acid and by oxidation of cyclopentanone by peracetic acid in acetic acid.
