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Hydroboration-Oxidation of Alkenes

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.

meta-Directing Deactivators: –NO2, –CN, –CHO, –&NoBreak;CO2R, –COR, –CO2H

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...

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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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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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Methyl 2-hydr-oxy-3-nitro-benzoate.

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¹Department of Chemistry, Nanchang University, Nanchang 330031, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study reveals the molecular structure of C(8)H(7)NO(5), highlighting an intramolecular hydrogen bond. The crystal structure also features intermolecular hydrogen bonding between molecules.

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Area of Science:

Crystallography
Molecular structure analysis
Organic chemistry

Background:

Understanding the three-dimensional arrangement of atoms in molecules is crucial for predicting chemical properties and reactivity.
Hydrogen bonding plays a significant role in molecular conformation and crystal packing.

Purpose of the Study:

To determine the precise molecular structure of the title compound, C(8)H(7)NO(5).
To investigate the presence and nature of intramolecular and intermolecular interactions within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to analyze the crystal structure.
Structural parameters were determined and analyzed to identify hydrogen bonding networks.

Main Results:

The title compound, C(8)H(7)NO(5), exhibits an approximately planar molecular conformation.
A significant intramolecular O-H⋯O hydrogen bond was identified between the hydroxyl and carboxylate groups.
Weak intermolecular C-H⋯O hydrogen bonds were also observed, contributing to the overall crystal packing.

Conclusions:

The molecular geometry and hydrogen bonding patterns of C(8)H(7)NO(5) have been elucidated.
The findings provide insights into the intermolecular forces governing the solid-state structure of this compound.