Oxidation of seven 1-methylbenzimidazole (MBI) derivatives (with pKa's ranging from 1.6 to 6.0) was carried out with m-chloroperoxybenzoic acid and structures of the products formed were identified. (Condensed benzene moiety-hydroxylated)-2-(m-chlorobenzyloxy)-MBIs and 2-oxo-MBIs were obtained from MBIs with pKa's of more than 5.6 and about 3.3, respectively.
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http://dx.doi.org/10.1016/s0960-894x(98)00082-1 | DOI Listing |
J Org Chem
January 2025
Center for Analysis and Synthesis, Department of Chemistry, Lund University, Lund SE 221 00, Sweden.
A diastereospecific synthesis of vicinally substituted 2-oxazolidinones from α,β-unsaturated lactams using -chloroperoxybenzoic acid is reported. Several highly substituted 2-oxazolidinones were obtained in 19-46% yields in a one-pot reaction with complete control over the relative stereochemistry. The proposed reaction sequence consists of a Baeyer-Villiger oxidation, an epoxidation, and a concerted rearrangement.
View Article and Find Full Text PDFChemistry
January 2025
Centro de Química Estrutural, Institute of Molecular Sciences, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001, Lisboa, Portugal.
Self-assembly synthesis of mixed-ligand (silsesquioxane/acetate) complex allows to isolate record high nuclear copper(II) Cu-cage (1). In the presence of two additional sodium ions, a unique molecular architecture, with triple combination of ligands (cyclic and acyclic silsesquioxanes as well as acetates), has been formed. The structure was established by single-crystal X-ray diffraction based on the use of synchrotron radiation.
View Article and Find Full Text PDFNanoscale
January 2025
Department of Materials Science, Institute of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8573, Japan.
This study reports the synthesis and characterisation of a ferrocene-based conjugated polymer and a chiral composite. The precursor copolymer was synthesised from 1,3-phenylenediamine and 1,1'-dibromoferrocene Buchwald-Hartwig polycondensation. This polymerisation process increased the effective conjugation length and led to magnetic spin interactions along the main chain, resulting in a ground triplet spin state at 25 °C.
View Article and Find Full Text PDFChemistry
January 2025
School of Chemistry and Chemical Engineering, Nanjing University, of Science and Technology, Xiaolingwei 200, Nanjing, Jiangsu, China.
The selective cleavage of C-N bonds in N-containing compounds holds significant research value in organic synthesis, particularly for the synthesis of promising polynitrogen species. For instance, the discovery of the cyclo-pentazolate (cyclo-N ) anion in 2017 as a result of cleavage of the C-N bond has sparked interest within the field of high energy density materials. However, previous methods using ferrous glycinate and m-chloroperoxybenzoic acid generated the cyclo-N anion in a low yield of 19.
View Article and Find Full Text PDFJ Org Chem
October 2024
Laboratory of Asymmetric Synthesis, College of Chemistry and Environmental Engineering, Chongqing University of Arts and Sciences, 319 Honghe Ave., Yongchuan, Chongqing 402160, P.R. China.
We have established a mild CuI-catalyzed selenylation of pyrrolo[2,1-]isoquinoline derivatives in the presence of CPBA (-chloroperoxybenzoic acid) at ambient temperature. Corresponding organoselenides have been prepared readily in 53-92% yields. This process can also be expanded to the modification of pyrroles, azaindole, and indoles, delivering the desired heterocyclic selenides in moderate to good yields.
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