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Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

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.

Hydroboration-Oxidation of Alkenes

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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.

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...

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...

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.

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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Updated: Mar 29, 2026

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials

Published on: May 15, 2015

Sulfurized metal borohydrides.

M Paskevicius¹, B Richter¹, M Polański²

¹Interdisciplinary Nanoscience Center (iNANO) & Institut for Kemi, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark. mark.paskevicius@gmail.com.

Dalton Transactions (Cambridge, England : 2003)

|December 1, 2015

Summary

This summary is machine-generated.

Metal borohydrides react rapidly with sulfur below 200°C, releasing significant pure hydrogen gas. This exothermic reaction forms novel metal-boron-sulfur compounds for energy and precursor applications.

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Area of Science:

Materials Science
Inorganic Chemistry
Chemical Engineering

Background:

Metal borohydrides are versatile chemical compounds.
Elemental sulfur is a readily available element.
Understanding reactions involving these materials is crucial for developing new applications.

Purpose of the Study:

To investigate the in situ reactions between metal borohydrides and elemental sulfur.
To characterize the reaction products and their properties.
To explore potential applications of the resulting compounds.

Main Methods:

In situ thermal treatment of metal borohydrides with elemental sulfur.
Calorimetry to measure reaction exothermicity.
Gas analysis to identify released products.
Characterization of solid products.

Main Results:

Highly exothermic reactions (up to 700 J g⁻¹) observed below 200°C.
Rapid hydrogen gas release, notably pure from sodium borohydride (NaBH4).
Formation of various metal-boron-sulfur (MBH4-S) compounds.

Conclusions:

The reaction between metal borohydrides and sulfur is a rapid, exothermic process yielding hydrogen gas and novel MBH4-S materials.
These MBH4-S compounds show promise for high-energy applications, hydrogen generation, and as precursors.
The purity of hydrogen released from NaBH4 is a significant finding.