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Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

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Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
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Preparation of Nitriles01:12

Preparation of Nitriles

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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

5.2K
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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Preparation of Amines: Reduction of Amides and Nitriles01:13

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3.3K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
3.3K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

7.2K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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Base-stabilized nitrilium ions as convenient imine synthons.

Tom van Dijk1, Martijn S Bakker1, Flip Holtrop1

  • 1†Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.

Organic Letters
|March 3, 2015
PubMed
Summary

Researchers developed a straightforward method to synthesize diverse substituted imines using stabilized N-alkylnitrilium triflates. These stable intermediates react with nucleophiles, yielding amidines and phosphaamidines efficiently.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • N-alkylnitrilium triflates are valuable precursors for imine synthesis.
  • These compounds are often thermally labile and difficult to handle.
  • Developing stable imine synthons is crucial for broader synthetic applications.

Purpose of the Study:

  • To present a simple and efficient methodology for synthesizing substituted imines.
  • To stabilize thermally labile N-alkylnitrilium triflates for easier handling.
  • To demonstrate the utility of these stabilized intermediates in synthesizing amidines and phosphaamidines.

Main Methods:

  • Stabilization of N-alkylnitrilium triflates using pyridine or DMAP.
  • Formation of moderately air-stable base-adducts.
  • Reaction of stabilized imine synthons with phosphorus- and nitrogen-based nucleophiles.

Main Results:

  • A wide range of substituted imines were synthesized efficiently.
  • Moderately air-stable imine synthons were successfully prepared.
  • The methodology provided convenient access to amidines and phosphaamidines.

Conclusions:

  • The presented methodology offers a simple and efficient route to substituted imines.
  • Base-stabilized N-alkylnitrilium triflate adducts serve as versatile imine synthons.
  • This approach facilitates the synthesis of amidines and phosphaamidines from readily available precursors.