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Carbocations

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...

Aromatic Hydrocarbon Anions: Structural Overview

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...

Anionic Chain-Growth Polymerization: Overview

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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

An anionic nucleophilic d⁴ carbyne complex.

Anthony F Hill¹, Richard Y Kong¹

¹Research School of Chemistry, Australian National University, Canberra, Australian Capital Territory ACT 2601, Australia. a.hill@anu.edu.au.

Chemical Communications (Cambridge, England)

|January 27, 2017

Summary

This summary is machine-generated.

Tungsten methylidyne complexes react with tert-butyllithium to form anionic neopentylidyne intermediates. These intermediates serve as nucleophiles, reacting with various electrophiles to yield new tungsten carbyne complexes.

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Area of Science:

Organometallic Chemistry
Tungsten Chemistry
Carbyne Complexes

Background:

Methylidyne complexes are versatile organometallic compounds.
Tungsten complexes with phosphine ligands are of significant synthetic interest.

Purpose of the Study:

To synthesize and characterize new tungsten carbyne complexes.
To explore the nucleophilic reactivity of anionic tungsten methylidyne intermediates.

Main Methods:

Reaction of [W(≡CH)Br(CO)2(dcpe)] with tert-butyllithium.
Nucleophilic addition of the resulting anionic complex to electrophiles such as alkyl halides, disulfides, and organotin chlorides.
Characterization of the synthesized carbyne complexes.

Main Results:

Formation of the anionic neopentylidyne complex Li[W(≡C^tBu)(CO)2(dcpe)].
Successful reaction of the anionic intermediate with tert-butyl chloride, tert-butyl bromide, diphenyl diselenide, diphenyl ditelluride, and trimethyltin chloride.
Synthesis of new tungsten carbyne complexes [W(≡C^tBu)(X)(CO)2(dcpe)] where X = Cl, Br, SePh, TePh, and SnMe3.

Conclusions:

Anionic tungsten neopentylidyne complexes can be generated and act as effective metal-based nucleophiles.
A range of new tungsten carbyne complexes with diverse substituents at the carbyne carbon have been synthesized.
This study expands the synthetic utility of tungsten methylidyne complexes.