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Preparation and Reactions of Thiols

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.

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.

Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

Preparation of Diols and Pinacol Rearrangement

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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Updated: May 7, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Two methods for spirothiohydantoin synthesis.

Neyko Stoyanov, Marin Marinov

Acta Chimica Slovenica

|September 25, 2013

Summary

This summary is machine-generated.

Two methods for synthesizing spirothiohydantoins were developed. These compounds were created using 1-aminocycloalkanecarboxylic acids with thiourea or by hydrolyzing spirodithiohydantoins, with structures confirmed via spectral analysis.

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Last Updated: May 7, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Published on: February 6, 2019

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

Published on: February 9, 2021

Area of Science:

Organic Chemistry
Medicinal Chemistry

Background:

Spirothiohydantoins are heterocyclic compounds with potential pharmaceutical applications.
Efficient synthesis routes are crucial for exploring their biological activities.

Purpose of the Study:

To present two novel synthetic methodologies for spirothiohydantoin derivatives.
To confirm the structures of the synthesized compounds using advanced spectroscopic techniques.

Main Methods:

Synthesis via the reaction of 1-aminocycloalkanecarboxylic acids with thiourea.
Synthesis via the hydrolysis of corresponding spirodithiohydantoins using barium hydroxide.
Structural elucidation using Nuclear Magnetic Resonance (1H, 13C NMR), Infrared (IR), and Mass Spectrometry (MS).

Main Results:

Successful synthesis of target spirothiohydantoin compounds using both described methods.
Confirmation of compound structures and purity through comprehensive spectral data analysis.
Demonstrated viability of two distinct synthetic pathways for spirothiohydantoin preparation.

Conclusions:

Established two effective and verifiable methods for spirothiohydantoin synthesis.
Provided a foundation for further research into the medicinal chemistry of these compounds.
Highlighted the utility of spectroscopic methods in structural characterization of novel heterocyclic compounds.