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Related Concept Videos

Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
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...
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.

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Related Experiment Video

Updated: May 22, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Rubrene endoperoxide acetone monosolvate.

Kiyoaki Shinashi, Akira Uchida

    Acta Crystallographica. Section E, Structure Reports Online
    |May 17, 2012
    PubMed
    Summary

    This study details the crystal structure of a photooxygenation product derived from rubrene (5,6,11,12-tetra-phenyl-tetra-cene). The molecule features a unique O-O bond and forms specific hydrogen bonds in its acetone solvate crystal structure.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Photochemistry

    Background:

    • Rubrene (5,6,11,12-tetra-phenyl-tetra-cene) is a well-known polycyclic aromatic hydrocarbon.
    • Photooxygenation reactions are crucial for understanding oxidative degradation and synthesis of organic molecules.

    Purpose of the Study:

    • To elucidate the crystal structure of the acetone solvate, a photooxygenation product of rubrene.
    • To analyze the molecular geometry, including the transannular O-O bond and dihedral angles.
    • To investigate intermolecular interactions within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, and intermolecular contacts (hydrogen bonds, dipolar interactions).

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    Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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    The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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    The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

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    Synthesis of a Water-soluble Metal–Organic Complex Array
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    Published on: October 8, 2016

    Main Results:

    • The structure of the rubrene photooxygenation product (1,3,10,12-tetra-phenyl-19,20-dioxapenta-cyclo-[10.6.2.0(2,11).0(4,9).0(13,18)]icosa-2(11),3,5,7,9,13,15,17-octa-ene acetone monosolvate) was determined.
    • A significant molecular bend was observed at the bridgehead atoms linked by an O-O transannular bond (dihedral angle of 49.21(6)°).
    • Rubrene molecules form columns via C-H⋯O hydrogen bonds, while acetone molecules form dimers through carbonyl-carbonyl dipolar interactions.

    Conclusions:

    • The crystal structure reveals the specific arrangement and bonding in the rubrene photooxygenation product.
    • Intermolecular C-H⋯O hydrogen bonds and carbonyl-carbonyl dipolar interactions play key roles in stabilizing the crystal packing.
    • This structural information provides insights into the reactivity and properties of rubrene derivatives.