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Preparation of Nitriles01:12

Preparation of Nitriles

2.8K
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...
2.8K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

5.1K
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.
5.1K
Nuclear Transmutation03:20

Nuclear Transmutation

20.9K
Nuclear transmutation is the conversion of one nuclide into another. It can occur by the radioactive decay of a nucleus, or the reaction of a nucleus with another particle. The first manmade nucleus was produced in Ernest Rutherford’s laboratory in 1919 by a transmutation reaction, the bombardment of one type of nuclei with other nuclei or with neutrons. Rutherford bombarded nitrogen-14 atoms with high-speed α particles from a natural radioactive isotope of radium and observed...
20.9K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

5.7K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
5.7K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.9K
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...
4.9K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.2K
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,...
3.2K

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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
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Conversion of Dinitrogen to Nitriles at a Multinuclear Titanium Framework.

Murali Mohan Guru1, Takanori Shima1,2, Zhaomin Hou3,4

  • 1Advanced Catalysis Research Group, RIKEN, Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.

Angewandte Chemie (International Ed. in English)
|September 10, 2016
PubMed
Summary

A novel titanium complex activates dinitrogen (N2) for nitrile synthesis. This method is compatible with various functional groups, offering a versatile platform for organic chemistry.

Keywords:
dinitrogen activationhydridesnitrilesorganometallicstitanium

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Area of Science:

  • Inorganic Chemistry
  • Organic Synthesis
  • Organometallic Chemistry

Background:

  • Nitrogen fixation and its conversion into valuable organic compounds remain a significant challenge in chemistry.
  • Developing efficient catalytic systems for dinitrogen (N2) activation is crucial for sustainable synthesis.

Purpose of the Study:

  • To report the synthesis of a tetranuclear titanium complex capable of activating dinitrogen (N2).
  • To demonstrate the utility of this complex as a platform for the synthesis of nitriles.

Main Methods:

  • Formation of a mixed diimide/dinitride tetranuclear titanium complex.
  • Utilizing the activated dinitrogen complex for nitrile synthesis through reactions with organic substrates.

Main Results:

  • Successful activation of dinitrogen (N2) by the tetranuclear titanium complex.
  • Efficient synthesis of nitriles using this unique platform.
  • Demonstrated compatibility with diverse functional groups, including aromatic C-X bonds (X=Cl, Br, I), nitro groups, and ammonia-sensitive moieties like aldehydes and chloromethyl groups.

Conclusions:

  • The mixed diimide/dinitride tetranuclear titanium complex is an effective platform for dinitrogen (N2) activation and subsequent nitrile synthesis.
  • The developed synthetic method exhibits broad functional group tolerance, making it a valuable tool in organic synthesis.