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Visible-Light-Induced Insertion of Siloxycarbene into Amide N-H Bonds: Synthesis of Carbinolamides from Acylsilanes and Amides.
J Org Chem
January 2025
Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
The insertion of carbene into secondary amide N-H bonds remains underexplored in organic synthesis. In this work, we discovered the visible-light-induced insertion of siloxycarbene into amide N-H bonds. This metal-free, facile reaction proceeds with atom economy under mild conditions with a broad range of secondary N-H amides, including benzanilide, acetanilide, oxindole, isatin, quinolinone, and maleimide, affording stable - and -acetals in excellent isolated yields.
View Article and Find Full Text PDFIntegrated analysis of cellulose structure and properties using solid-state low-field H-NMR and photoacoustic spectroscopy.
Sci Rep
January 2025
Nonprofitable Organization Touche NPO, Sapporo, 060-004, Japan.
In this study, we explore the structural intricacies of cellulose, a polymer composed of glucose monomers arranged in a linear chain, primarily investigated through solid-state NMR techniques. Specifically, we employ low-field proton nuclear magnetic resonance (H-NMR) to delve into the diverse hydrogen atom types within the cellulose molecule. The low-field H-NMR technique allows us to discern these hydrogen atoms based on their distinct chemical shifts, providing valuable insights into the various functional groups present in cellulose.
View Article and Find Full Text PDFVisible-Light-Induced Synthesis of Esters via a Self-Propagating Radical Reaction.
J Org Chem
January 2025
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China.
We herein disclose a visible-light-induced synthesis of aryl esters through the cross-dehydrogenative coupling of aldehydes with phenols using BrCCl, in which phenolate functions as both a substrate and a photosensitizer. This transition-metal- and photocatalyst-free visible-light-induced esterification is suitable for a wide range of substrates and gives moderate to excellent yields (up to 95%). Mechanistic studies provided evidence of a self-propagating radical reaction involving homolytic cleavage of the aldehydic C-H bond and the formation of acyl bromides.
View Article and Find Full Text PDFOxygen, light, and mechanical force mediated radical polymerization toward precision polymer synthesis.
Chem Commun (Camb)
January 2025
State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Science, Fudan University, Shanghai 200438, China.
The synthesis of polymers with well-defined composition, architecture, and functionality has long been a focal area of research in the field of polymer chemistry. The advancement of controlled radical polymerization (CRP) has facilitated the synthesis of precise polymers, which are endowed with new properties and functionalities, thereby exhibiting a wide range of applications. However, radical polymerization faces several challenges, such as oxygen intolerance, and common thermal initiation methods may lead to side reactions and depolymerization.
View Article and Find Full Text PDFVisible-Light-Induced Annulation of Benzothioamides with Sulfoxonium Ylides To Construct Thiazole Derivatives.
Org Lett
January 2025
Innovation Center for Chemical Sciences, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou Industrial Park, Suzhou, Jiangsu 215123, China.
Herein, visible-light-induced annulation of benzothioamides with sulfoxonium ylides to furnish thiazole derivatives is developed under transition-metal-, photocatalyst-, and oxidant-free conditions. This protocol exhibits good substrate scope, affording the desired products with satisfied yields in a mild and green manner. Detailed mechanistic studies suggest that the benzothioamide substrate plays a dual role in this reaction.
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