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meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
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Nitriles to Amines: LiAlH4 Reduction00:55

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Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Neutral Fe(IV) alkylidenes, including some that bind dinitrogen.

Brian M Lindley1, Brian P Jacobs, Samantha N MacMillan

  • 1Department of Chemisty & Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853, USA. ptw2@cornell.edu.

Chemical Communications (Cambridge, England)
|December 16, 2015
PubMed
Summary

Neutral iron(IV) alkylidene complexes were synthesized for potential use in olefin metathesis catalysis. Nucleophilic attack on an imine precursor yielded these novel iron species, advancing catalyst development.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Olefin metathesis is a crucial reaction in organic synthesis.
  • Development of novel catalysts is essential for improving reaction efficiency and scope.
  • Iron-based catalysts offer a more sustainable alternative to precious metal catalysts.

Purpose of the Study:

  • To synthesize neutral, formally Fe(IV) alkylidene species.
  • To explore their potential as olefin metathesis catalysts.
  • To investigate the reactivity of iron complexes with various nucleophiles.

Main Methods:

  • Synthesis of cationic iron precursor: [mer-{κ-C,N,C-(C6H4-yl)-2-CH=N(2-C6H4-C(iPr)=)}Fe(PMe3)3][B(3,5-CF3-C6H3)4].
  • Nucleophilic attack using organolithium and potassium reagents (MeLi, PhCH2K, 2-picolyllithium, Me2PCH2Li, MePhPCH2Li, Ph2PCH2Li) at the imine functionality.
  • Reactions with Grignard (MeMgCl) and organolithium (mesityllithium) reagents to study alternative reactivity.

Main Results:

  • Successful synthesis of neutral Fe(IV) alkylidene complexes via nucleophilic addition to the imine.
  • Demonstration of distinct reactivity pathways based on the nucleophile used.
  • Structural characterization of key intermediates and products, including mer-{κ-C,N,C-(C6H4-yl)-2-CH(Bn)N(2-C6H4-C(iPr))}Fe{trans-(PMe3)2}N2 and {κ-C,N,C,P-(C6H4-yl)-2-CH(CH2PMe2)N(2-C6H4-C(iPr)=)}Fe(PMe3)2.

Conclusions:

  • Neutral Fe(IV) alkylidene complexes can be accessed through nucleophilic attack on imine precursors.
  • These complexes represent a new class of potential olefin metathesis catalysts.
  • Understanding the reactivity of different nucleophiles is key to controlling the outcome of these iron-mediated transformations.