Unexpected Ring Opening During the Imination of Camphor‐Type Bicyclic Ketones

Abstract

A new ring opening reaction was found while attempting to isolate the imines from ortho-heteroatom substituted anilines and camphor-like bicyclic ketones. The benzoazoles containing a cyclopentanemethyl group at position 2 of the heterocycle were isolated instead of the expected imines. The detailed study of the transformation, including EPR experiments, revealed the most probable radical mechanism. The proposed reaction pathways were confirmed by quantum chemical calculations. The dichotomy of 1-2 and 2-3 bonds cleavage is discussed together with the evaluation of the stereochemical outcome of the reactions. The benzoazoles obtained via the new reaction are of particular interest for the medicinal chemistry.

Vanadyl porphyrin – efficient spin probe to study the alumina surface of supported catalysts in situ

“…Electron paramagnetic resonance spectroscopy is a powerful tool for the investigation of the local environment of paramagnetic species/spin probes in various media [1][2][3]. It provides exclusive opportunities to study in situ the processes in complex multicomponent media [4][5][6], and the peculiarities of catalytic reactions and catalysts [7,8]. Among the various types of spin probes that can be successfully employed in the elds of catalysis, biochemistry and related areas, vanadyl occupy a distinctive position, as it forms strong anionic, cationic, and neutral complexes with all types of ligands.…”

Synthesis and Structural Characterization of Palladium(II) Mixed-Ligand Complexes of N-(Benzothiazol-2-yl)benzamide and 1,2-Bis(diphenylphosphino)ethane

“…Benzothiazoles are important bicyclic organic compounds that are used in organic synthesis 1,2 or as important ligands in the synthesis of metallic complexes. 3,4 Typically, benzothiazoles used in the inorganic field possess effective donor atoms and mostly coordinate in a monodentate manner through the nitrogen atom 5,6 or sometimes through the sulfur atom.…”

“…Benzothiazoles are important bicyclic organic compounds that are used in organic synthesis , or as important ligands in the synthesis of metallic complexes. , Typically, benzothiazoles used in the inorganic field possess effective donor atoms and mostly coordinate in a monodentate manner through the nitrogen atom , or sometimes through the sulfur atom . The importance of benzothiazoles as ligands is increased through benzothiazole derivatives containing additional donor atoms, such as nitrogen, sulfur, or oxygen, that can coordinate bidentately through two nitrogen atoms , or nitrogen and oxygen atoms …”