Related Experiment Video
Updated: Jun 5, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
(E)-Dimethyl 2-(6-benzoyl-7-hydr-oxy-4-methoxy-carbonyl-2-oxo-2H-chromen-8-yl)but-2-enedioate
Robabeh Baharfar1, S Mohammad Vahdat, S Meysam Baghbanian
1Department of Chemistry, University of Mazandaran, 47415 Babolsar, Iran.
Abstract:
The mol-ecule of the title compound, C(24)H(18)O(10), a previously unknown coumarin derivative, contains methoxy-carbonyl, 2-butenedioate and benzoyl groups aligned at angles of 28.04 (2), 76.89 (3) and 42.48 (13)°, respectively, to the plane of the coumarin ring system. Intra-molecular O-H⋯O hydrogen bonding between hydr-oxy and carbonyl groups and weak inter-molecular C-H⋯O hydrogen bonding is present in the crystal structure. The two carbon atoms and attached H atom of the ethylene bond are disordered over two positions, with site occupancy factors of ca 0.9 and 0.1.
Related Concept Videos
Hydroboration-Oxidation of Alkenes
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
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...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

