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Preparation and Reactions of Sulfides

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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.

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

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The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...

Stability of Conjugated Dienes

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Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

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Updated: Apr 28, 2026

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Published on: August 20, 2018

Stepwise synthesis of a stable diphosphasilirane and its unexpected dimerization.

Kirsten Reuter¹, Carsten von Hänisch

¹Fachbereich Chemie and Wissenschaftliches Zentrum für Materialwissenschaften (WZMW), Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043 Marburg, Germany. haenisch@chemie.uni-marburg.de.

Chemical Communications (Cambridge, England)

|June 6, 2014

Summary

Researchers synthesized a thermally stable bicyclic diphosphasilirane compound. However, low-temperature storage led to rearrangement into a dimeric species due to impurities.

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

Area of Science:

Organosilicon Chemistry
Main Group Chemistry

Background:

Cyclic diphosphanides are versatile precursors in inorganic synthesis.
Diphosphasiliranes represent an intriguing class of silicon-containing heterocycles.

Purpose of the Study:

To synthesize a novel thermally stable bicyclic diphosphasilirane.
To investigate the stability and potential rearrangement pathways of the synthesized compound.

Main Methods:

Oxidation of alkaline earth metal substituted cyclic diphosphanide (3) using 1,2-dibromoethane.
Characterization of the synthesized bicyclic diphosphasilirane (4).
Monitoring the compound's stability under low-temperature storage conditions.

Main Results:

Successful synthesis of the bicyclic diphosphasilirane O(SiiPr2P)2SiiPr2 (4).
Observation of impurity-induced rearrangement to a dimeric species [O(SiiPr2P)2SiiPr2]2 (5) upon prolonged low-temperature storage.

Conclusions:

The synthesized bicyclic diphosphasilirane exhibits thermal stability under standard conditions.
Impurities can trigger rearrangement to dimeric forms, impacting long-term stability.