The direct alkylation of 1,3-dicarbonyl compounds with benzylic alcohols is shown to be efficiently catalyzed by simple Brønsted acids such as triflic acid (TfOH) and p-toluenesulfonic acid (PTS) to give rise to monoalkylated dicarbonyl derivatives in high yields. In the absence of the nucleophile, substituted alkenes, generated through a formal dimerization reaction, are obtained. The reactions are carried out in air using undried solvents, with water being the only side product of the process.
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http://dx.doi.org/10.1021/ol070624a | DOI Listing |
Molecules
December 2024
"C. D. Nenitzescu" Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, 060023 Bucharest, Romania.
Azulene-1,3-bis(semicarbazone), , and azulene-1,3-bis(thiosemicarbazone), , were synthesized by the acid-catalyzed condensation reactions of semicarbazide and thiosemicarbazide, respectively, with azulene-1,3-dicarboxaldehyde in stoichiometric amounts. Compounds and were identified by high-resolution mass spectrometry and characterized by IR, H-NMR, C-NMR, and UV-vis spectroscopic techniques. Crystal structure determination of azulene-1,3-bis(thiosemicarbazone) shows that the thiosemicarbazone units exhibit a -closed conformation, with both arms oriented in the same direction and adopting an configuration with respect to the imine linkages.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Organisch-Chemisches Institut, Universität Münster, Corrensstraße 40, 48149 Münster, Germany.
Herein we report a simple BF-catalyzed cycloaddition of dihydropyridines with bicyclobutanes for the expedient synthesis of novel three-dimensional azacycle-fused bicyclo[2.1.1]hexane scaffolds.
View Article and Find Full Text PDFJ Chem Phys
December 2024
Department of Materials Science and Engineering, University of Michigan, Ann Arbor, Michigan 48109, USA.
Organic-inorganic hybrid materials are explored for application as solid electrolytes for lithium-ion batteries. The material consists of a porous silica network, of which the pores are infiltrated by poly(ethylene oxide) and lithium perchlorate. The synthesis involves two steps: First, the inorganic backbone is created by the acid-catalyzed sol-gel synthesis of tetraethyl orthosilicate to ensure continuity of the backbone in three dimensions.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, United States.
A Brønsted acid-catalyzed enantioselective synthesis of ()-1,3-butadienyl-2-carbinols is developed. By employing a chiral phosphoric acid as the catalyst, a variety of 1,3-butadienyl-2-carbinols were obtained in good yields with excellent -selectivities and enantiopurities from α-alkyl-substituted homoallenyl boronates.
View Article and Find Full Text PDFBiomolecules
December 2024
Department of Pharmacy, Division of Pharmacognosy and Natural Products Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15771 Athens, Greece.
24-Masticadienonic acid (MNA) and 24-isomasticadienonic acid (IMNA) are the major triterpenic acids in Chios Mastic Gum (CMG), a resin derived from var. . Despite their promising pharmacological potential, limited information is available due to the complexity of isolating them in pure form.
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