Related Experiment Video
Updated: Jun 1, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
2-(1H-Benzimidazol-1-yl)-1-(2-furyl)ethanone O-propyloxime
Abstract:
In the mol-ecule of the title compound, C(16)H(17)N(3)O(2), the planar benzimidazole ring system [maximum deviation = 0.013 (1) Å] is oriented at a dihedral angle of 75.32 (4)° with respect to the furan ring. An intra-molecular C-H⋯O inter-action results in the formation of a planar six-membered ring [maximum deviation = 0.019 (15) Å], which is oriented at a dihedral angle of 1.91 (3)° with respect to the adjacent furan ring. In the crystal structure, inter-molecular C-H⋯N inter-actions link the mol-ecules into centrosymmetric R(2) (2)(18) dimers. In addition, the structure is stabilized by π-π contacts between the imidazole rings [centroid-centroid distance = 3.5307 (8) Å] and weak C-H⋯π inter-actions.
Related Concept Videos
Structure and Nomenclature of Epoxides
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Structure and Nomenclature of Ethers
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
Autoxidation of Ethers to Peroxides and Hydroperoxides
Crown Ethers
Base-Catalyzed Ring-Opening of Epoxides

