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Selective Oxidation of Alcohols to Carbonyls Under Decatungstate-Mediated Photoelectrochemical Conditions.
Chemistry
November 2024
PhotoGreen Lab, Department of Chemistry, University of Pavia, viale Taramelli 12, 27100, Pavia, Italy.
The oxidation of alcohols to the corresponding carbonyl derivatives has been realized under photoelectrochemical conditions in the presence of tetrabutylammonium decatungstate (TBADT) as the homogeneous photocatalyst. The protocol can be applied to both primary and secondary, benzylic and aliphatic alcohols. The desired products are obtained selectively, skipping the need for purposely added chemical oxidants.
View Article and Find Full Text PDFC═N Bond Ozonolysis and β-Scission: A Breakthrough Approach to the Synthesis of ω-Functionalized Compounds from Carbonyl Derivatives.
Org Lett
September 2024
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow 119991, Russian Federation.
This work discloses a two-step, one-pot approach to ω-functionalized esters via cleavage of the alicyclic fragment of cycloalkanone semicarbazones. This approach is based on a combination of the synthesis of various alkoxyhydroperoxides via cycloalkanone semicarbazone ozonolysis and interaction of these peroxides with transition metal salts, leading to cleavage of the aliphatic cycle and subsequent ω-functionalized ester formation. A broad series of ω-halogen or pseudohalogen esters have been successfully synthesized in yields ranging from 23 to 73% per starting semicarbazone.
View Article and Find Full Text PDFManganese-Catalyzed Hydrogenation of Amides and Polyurethanes: Is Catalyst Inhibition an Additional Barrier to the Efficient Hydrogenation of Amides and Their Derivatives?
Organometallics
January 2024
EaStCHEM, School of Chemistry, University of St. Andrews, North Haugh, St. Andrews KY16 9ST, U.K.
The hydrogenation of amides and other less electrophilic carbonyl derivatives with an N-C=O functionality requires significant improvements in scope and catalytic activity to be a genuinely useful reaction in industry. Here, we report the results of a study that examined whether such reactions are further disadvantaged by nitrogen-containing compounds such as aliphatic amines acting as inhibitors on the catalysts. In this case, an enantiomerically pure manganese catalyst previously established to be efficient in the hydrogenation of ketones, -aryl-imines, and esters was used as a prototype of a manganese catalyst.
View Article and Find Full Text PDFAsymmetric Fe-Catalyzed Thia-Michael Addition Reaction to α,β-Unsaturated Oxazolidin-2-one Derivatives.
Org Lett
December 2017
Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC G1V 0A6, Canada.
A highly enantioselective Fe-catalyzed thia-Michael addition to α,β-unsaturated carbonyl derivatives was developed. The scope of the reaction was demonstrated with a selection of aromatic, heterocyclic and aliphatic thiols, and various Michael acceptors. The corresponding β-thioethers were obtained in good to excellent yields (up to 98%) and moderate to excellent enantioselectivities (up to 96:4 er).
View Article and Find Full Text PDFInter- and intramolecular CF···C=O interactions on aliphatic and cyclohexane carbonyl derivatives.
J Comput Chem
January 2016
School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY169ST, United Kingdom.
Weak inter- and intra- molecular C(δ+)F(δ-)···C(δ+)=O(δ-) interactions were theoretically evaluated in 4 different sets of compounds at different theoretical levels. Intermolecular CH3F···C=O interactions were stabilizing by about 1 kcal mol(-1) for various carbonyl containing functional groups. Intramolecular CF···C=O interactions were also detected in aliphatic and fluorinated cyclohexane carbonyl derivatives.
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