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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.

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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

Hybridization of Atomic Orbitals I

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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

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Oxybis(dimesitylborane) dichloro-methane hemisolvate.

Jung-Ho Son¹, James D Hoefelmeyer

¹Department of Chemistry, The University of South Dakota, 414 E. Clark St, Vermillion, SD 57069, USA.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the crystal structure of a boron-containing compound, revealing linear O-B-O linkages and orthogonal trigonal planar boron centers. Intermolecular C-H⋯π interactions and dichloromethane solvent molecules were also observed.

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Area of Science:

Inorganic Chemistry
Crystallography
Supramolecular Chemistry

Background:

Boron compounds exhibit diverse structural motifs and bonding.
Understanding intermolecular interactions is crucial for materials science.
Solvent molecules can influence crystal packing and molecular geometry.

Purpose of the Study:

To characterize the crystal structure of the title compound, C(36)H(44)B(2)O·0.5CH(2)Cl(2).
To analyze the coordination geometry around the boron centers.
To investigate intermolecular interactions within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction analysis was employed.
Geometric parameters, including bond angles and interplanar angles, were precisely determined.
Intermolecular contacts were identified and quantified.

Main Results:

The compound features an almost linear O-B-O linkage (177.23°).
Trigonal planar boron centers display approximately orthogonal arrangements.
Intermolecular C-H⋯π interactions between mesityl groups were observed (C-H⋯centroid distance of 3.6535 Å).
Dichloromethane solvent molecules occupy twofold rotation axes.

Conclusions:

The observed B-O-B geometry is consistent with previous findings for non-solvated structures.
The crystal structure is stabilized by significant intermolecular C-H⋯π interactions.
The presence of dichloromethane solvent molecules influences the overall crystal packing.