57825-33-9Relevant articles and documents
Conversion of InP Clusters to Quantum Dots
Friedfeld, Max R.,Johnson, Dane A.,Cossairt, Brandi M.
, p. 803 - 810 (2019)
Understanding and deconvoluting the different mechanisms involved in the synthesis of nanomaterials is necessary to make uniform materials with desirable function. In this study, in situ spectroscopic methods were used to study exchange reactions at the s
Investigation on the stoichiometry of carbon dioxide in isotope-exchange reactions with phenylacetic acids
Talbot, Alex,Sallustrau, Antoine,Goudet, Amélie,Taran, Frédéric,Audisio, Davide
supporting information, p. 171 - 176 (2021/08/10)
The functionalization of carbon dioxide (CO 2) as a C1 building block has attracted enormous attention. Carboxylation reactions, in particular, are of major interest for applications in isotope labeling. Due to the inexpensive nature of CO 2, information about its stoichiometric use is generally unavailable in the literature. Because of the rarity and limited availability of CO 2isotopomers, this parameter is of concern for applications in carbon-isotope labeling. We investigated the effects of the stoichiometry of labeled CO 2on carbon isotope exchange of phenyl? acetic acids. Both thermal and photocatalytic procedures were studied, providing insight into product outcome and isotope incorporation. Preliminary results on isotope-dilution effects of carbonate bases in photocatalytic carboxylation reactions have also been obtained.
Photochemical Strategy for Carbon Isotope Exchange with CO2
Babin, Victor,Talbot, Alex,Labiche, Alexandre,Destro, Gianluca,Del Vecchio, Antonio,Elmore, Charles S.,Taran, Frédéric,Sallustrau, Antoine,Audisio, Davide
, p. 2968 - 2976 (2021/03/09)
A photocatalytic approach for carbon isotope exchange is reported. Utilizing [13C]CO2 and [14C]CO2 as primary C1 sources, this protocol allows the insertion of the desired carbon isotope into phenyl acetic acids without the need for structural modifications or prefunctionalization in one single step. The exceptionally mild conditions required for this traceless transformation are in stark contrast with those for previous methods requiring the use of harsh thermal conditions.
Fast Carbon Isotope Exchange of Carboxylic Acids Enabled by Organic Photoredox Catalysis
Kong, Duanyang,Munch, Maxime,Qiqige, Qiqige,Cooze, Christopher J. C.,Rotstein, Benjamin H.,Lundgren, Rylan J.
supporting information, p. 2200 - 2206 (2021/02/16)
Carbazole/cyanobenzene photocatalysts promote the direct isotopic carboxylate exchange of C(sp3) acids with labeled CO2. Substrates that are not compatible with transition-metal-catalyzed degradation-reconstruction approaches or prone to thermally induced reversible decarboxylation undergo isotopic incorporation at room temperature in short reaction times. The radiolabeling of drug molecules and precursors with [11C]CO2 is demonstrated.
Direct reversible decarboxylation from stable organic acids in dimethylformamide solution
Kong, Duanyang,Moon, Patrick J.,Lui, Erica K.J.,Bsharat, Odey,Lundgren, Rylan J.
, p. 557 - 561 (2020/09/02)
Many classical and emerging methodologies in organic chemistry rely on carbon dioxide (CO2) extrusion to generate reactive intermediates for bond-forming events. Synthetic reactions that involve the microscopic reverse-the carboxylation of reactive intermediates-have conventionally been undertaken using very different conditions. We report that chemically stable C(sp3) carboxylates, such as arylacetic acids and malonate half-esters, undergo uncatalyzed reversible decarboxylation in dimethylformamide solution. Decarboxylation-carboxylation occurs with substrates resistant to protodecarboxylation by Br?nsted acids under otherwise identical conditions. Isotopically labeled carboxylic acids can be prepared in high chemical and isotopic yield by simply supplying an atmosphere of 13CO2 to carboxylate salts in polar aprotic solvents. An understanding of carboxylate reactivity in solution enables conditions for the trapping of aldehydes, ketones, and a,b-unsaturated esters.
Palladium-Catalyzed Carbon Isotope Exchange on Aliphatic and Benzoic Acid Chlorides
Gauthier, Donald R.,Rivera, Nelo R.,Yang, Haifeng,Schultz, Danielle M.,Shultz, C. Scott
supporting information, p. 15596 - 15600 (2018/11/23)
An operationally simple protocol for a palladium-catalyzed 13CO and 14CO exchange with activated aliphatic and benzoic carbonyls is presented. Several 13C and 14C building blocks, natural product derivatives, an
Partial oxygen migration in the photochemical wolff rearrangement - α-Oxocarben-Oxiren-isomerization or intermolecular mechanism?
Haiss, Peter,Zeller, Klaus-Peter
, p. 595 - 605 (2007/10/03)
Crossover experiments between isotopomeric species of 2-diazo-1-oxo-1-phenylethane (18O, 13C, D) establish beyond doubt that the oxygen migration accompanying the photochemical Wolff rearrangement is not the result of intermolecular
Study of the mechanism of base induced dehydrobromination of trans-β-bromostyrene
Ma?kosza, Mieczys?aw,Chesnokov, Alexey A.
, p. 1995 - 2000 (2007/10/03)
Observation that rates of dehydrobromination of trans-β-bromostyrene (1) and the Hofmann degradation of tetrabutyl ammonium cation depend on strength of base in different ways and that treatment of 1 with base results in fast abstraction of the β-proton imply the possibility that the dehydrobromination of 1 could proceed via α-elimination and Ph migration. In order to clarify this question, β-13C-labeled 1 was obtained and subjected to PTC dehydrobromination which proceeds without migration of Ph. The obtained results are consistent with an irreversible E1cB mechanism.
A plausible chemical analogy for biosynthesis of 2-arylbenzofuran of isoflavonoid origin and its application to synthesis of vignafuran
Kinoshita, Takeshi
, p. 259 - 262 (2007/10/03)
Treatment of 2-hydroxy-isoflav-3-ene with acid afforded 2-arylbenzofuran in good yield, and a mechanism for this chemical conversion involving loss of one carbon unit was described. This reaction scheme was suggested as a plausible chemical analogy for th
Chiral Organometallic Reagents, XVI. Enantiomerization of α-Thio-, α-Seleno-, and α-Telluro-Substituted Alkyllithium Compounds; Kinetic and Mechanistic Studies
Hoffmann, Reinhard W.,Dress, Ruprecht K.,Ruhland, Thomas,Wenzel, Andreas
, p. 861 - 870 (2007/10/02)
The rate of enantiomerization of the racemic α-phenylselenoalkyllithium compound 6 has been determined by dynamic NMR spectroscopy in THF.The enantiomerization rate was found to be first order with respect to monomeric 6 and to show no conspicuous sol
