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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.

Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

Properties of Organometallic Compounds

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Related Experiment Video

Updated: Jul 26, 2025

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

A Metallabicycle From Thiocarbonyl-Cyclopropenium Coupling.

Lachlan J Watson¹, Anthony F Hill¹

¹Research School of Chemistry, Australian National University, Sullivans Creek Road, Canberra, ACT, Australia.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|June 16, 2023

Summary

Researchers synthesized novel bicyclic metallathiapyrylium compounds from a rhodium thiocarbonyl complex and triphenylcyclopropenium bromide. These unique heterocycles exhibit interesting reactivity with silver triflate and halide ions.

Keywords:

cyclopropenium metalla-aromaticity metallacycle thiapyrylium thiocarbonyl

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

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Published on: March 20, 2017

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Last Updated: Jul 26, 2025

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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

Area of Science:

Organometallic Chemistry
Coordination Chemistry
Heterocyclic Chemistry

Background:

Thiocarbonyl complexes of rhodium are valuable precursors in organometallic synthesis.
Cyclopropenium salts offer unique reactivity due to their strained three-membered ring structure.
The development of novel heterocyclic compounds with metal-metal or metal-ligand bonding is an active area of research.

Purpose of the Study:

To synthesize and characterize novel bicyclic metallathiapyrylium compounds.
To investigate the reactivity of these new heterocycles with electrophilic reagents.
To explore the potential for metal-free isolobal analogues.

Main Methods:

Reaction of [RhCl(CS)(PPh3)2] with triphenylcyclopropenium bromide.
Halide abstraction using silver triflate (AgOTf) in acetonitrile.
Characterization of the resulting products using spectroscopic techniques and X-ray crystallography.

Main Results:

Successful synthesis of novel bicyclic metallathiapyrylium complexes, [Rh(κ2-C,S-C5S2Ph3)(PPh3)2X2] (X=Cl, Br).
These heterocycles represent a new class of compounds with no known metal-free isolobal precedent.
Reactions with AgOTf yielded a silver-containing salt, which could be converted back to the original rhodium complex upon treatment with NaCl.

Conclusions:

The study demonstrates the successful synthesis of unprecedented bicyclic metallathiapyrylium heterocycles.
The reactivity of these complexes with silver triflate highlights their potential as intermediates in further synthetic transformations.
The findings expand the scope of rhodium-mediated heterocyclic chemistry.