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Related Concept Videos

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.
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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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...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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.

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    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the crystal structure of (E)-2,3′,4,5-tetramethoxy-stilbene, revealing its near-planar geometry and weak intermolecular interactions. The findings highlight C-H⋯O hydrogen bonds and π-π stacking, crucial for understanding molecular packing in stilbene derivatives.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Materials Science

    Background:

    • Stilbene derivatives are important in various scientific fields.
    • Understanding the solid-state structure is key to predicting material properties.

    Purpose of the Study:

    • To elucidate the crystal structure of (E)-2,3′,4,5-tetramethoxy-stilbene.
    • To investigate the intermolecular interactions and packing in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction analysis.
    • Analysis of intermolecular interactions (hydrogen bonds, π-π stacking).

    Main Results:

    • The molecule (E)-2,3′,4,5-tetramethoxy-stilbene is virtually planar with a 4.06° angle between benzene rings.
    • Weak intermolecular interactions, including C-H⋯O hydrogen bonds and C-H⋯π interactions, were identified.
    • Molecules are arranged in planes parallel to (01) with a 3.3 Å spacing, suggesting plausible π-π electron interactions.

    Conclusions:

    • The crystal structure of (E)-2,3′,4,5-tetramethoxy-stilbene is characterized by a near-planar conformation.
    • Weak intermolecular forces govern the solid-state packing, with potential for π-π stacking.
    • These structural insights are valuable for designing related organic materials.