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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.

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

Alcohols from Carbonyl Compounds: Reduction

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

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.

Sugars as Energy Storage Molecules

Sugars as Energy Storage Molecules

Sugar (a simple carbohydrate) metabolism (chemical reactions) is a classic example of the many cellular processes that use and produce energy. Living things consume sugar as a major energy source because sugar molecules have considerable energy stored within their bonds. Consumed carbohydrates have their origins in photosynthesizing organisms like plants. During photosynthesis, plants use the energy of sunlight to convert carbon dioxide gas into sugar molecules, like glucose. Because this...

Common Ion Effect

Common Ion Effect

Compared with pure water, the solubility of an ionic compound is less in aqueous solutions containing a common ion (one also produced by dissolution of the ionic compound). This is an example of a phenomenon known as the common ion effect, which is a consequence of the law of mass action that may be explained using Le Châtelier’s principle. Consider the dissolution of silver iodide:

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Updated: Dec 17, 2025

Thermal Scanning Conductometry TSC as a General Method for Studying and Controlling the Phase Behavior of Conductive Physical Gels

Thermal Scanning Conductometry TSC as a General Method for Studying and Controlling the Phase Behavior of Conductive Physical Gels

Published on: January 23, 2018

Boron Effect on Sugar-Based Organogelators.

Andreas D Ludwig¹, Arnaud Saint-Jalmes², Cristelle Mériadec²

¹Ecole Nationale Supérieure de Chimie de Rennes, CNRS, ISCR-UMR6226, Université de Rennes, 35000, Rennes, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|June 25, 2020

Summary

This summary is machine-generated.

New alkylglucoside phenyl boronate derivatives form organogels at low concentrations. These water-sensitive gels, unlike stable counterparts, offer potential for smart topical drug delivery systems.

Keywords:

alkylglucosides boronates glycolipids organogels water sensitive

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Preparation of Biopolymer Aerogels Using Green Solvents

Preparation of Biopolymer Aerogels Using Green Solvents

Published on: July 4, 2016

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Thermal Scanning Conductometry TSC as a General Method for Studying and Controlling the Phase Behavior of Conductive Physical Gels

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Preparation of Biopolymer Aerogels Using Green Solvents

Preparation of Biopolymer Aerogels Using Green Solvents

Published on: July 4, 2016

Area of Science:

Materials Science
Organic Chemistry
Supramolecular Chemistry

Background:

Organogelators are crucial for developing soft materials.
Alkylglucosides and phenyl boronic acid are known chemical entities.
Acetal-based organogelators are stable but lack responsiveness.

Purpose of the Study:

To synthesize novel alkylglucoside phenyl boronate derivatives.
To investigate their organogelation properties in organic solvents.
To explore their potential for stimuli-responsive applications, such as drug delivery.

Main Methods:

Synthesis of alkylglucoside phenyl boronate derivatives via reaction with phenyl boronic acid.
Gelation studies in various organic solvents at low concentrations.
Rheological measurements to characterize mechanical properties.
Scanning Electron Microscopy (SEM) and Small-Angle X-ray Scattering (SAXS) for morphology and self-assembly analysis.
Hydrolysis studies to assess water sensitivity.

Main Results:

Successful synthesis of alkylglucoside phenyl boronate derivatives.
Effective gelation of organic solvents at low amphiphile concentrations.
Characterization of gels as elastic solids with specific morphologies and self-assembly structures.
Demonstration of rapid gel disruption upon addition of a small amount of water (5% v/v).
Identification of hydrolysis products as the original alkylglucoside and phenyl boronic acid.

Conclusions:

Alkylglucoside phenyl boronate derivatives are effective organogelators.
These boronated organogels exhibit significant water sensitivity, unlike stable acetal-based systems.
The water-triggered disassembly suggests potential for smart soft materials.
These compounds are promising candidates for topical drug delivery applications requiring controlled release.