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Related Concept Videos

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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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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1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

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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.
5.2K
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
7.9K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

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4.3K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
4.3K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

4.0K
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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A novel thiourea type organocatalyst possessing a single NH functionality.

Predrag Jovanovic1, Milos Petkovic1, Milena Simic1

  • 1University of Belgrade, Faculty of Pharmacy, Department of Organic Chemistry, Vojvode Stepe 450, 11221 Belgrade, Serbia. vladimir.savic@pharmacy.bg.ac.rs.

Organic & Biomolecular Chemistry
|June 18, 2016
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Summary

A new thiourea organocatalyst was developed using a modified H-bonding pattern and a specific phenyl motif. This catalyst efficiently produces products from alpha-amination and Michael reactions with high stereoselectivity.

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Area of Science:

  • Organic Chemistry
  • Catalysis

Background:

  • Thiourea derivatives are widely used as organocatalysts.
  • Modifying H-bonding patterns can enhance catalyst performance.

Purpose of the Study:

  • To design and synthesize a novel thiourea organocatalyst.
  • To investigate its efficacy in stereoselective synthesis.

Main Methods:

  • Rational design of a thiourea catalyst incorporating a 3,5-bis(trifluoromethyl)phenyl group.
  • Application of the catalyst in alpha-amination and Michael reactions.

Main Results:

  • The novel catalyst demonstrated excellent yields in both reaction types.
  • High levels of stereoselectivity were achieved in the product formation.

Conclusions:

  • The designed thiourea organocatalyst shows significant potential for stereoselective synthesis.
  • This work may open new avenues for thiourea-based organocatalysis.