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Related Concept Videos

Preparation of Nitriles01:12

Preparation of Nitriles

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...
Protecting Groups for Aldehydes and Ketones: Introduction01:23

Protecting Groups for Aldehydes and Ketones: Introduction

Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.
Protection of Alcohols02:31

Protection of Alcohols

This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

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

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

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 the...

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

A novel protecting group methodology for syntheses using nitroxides.

Benjamin A Chalmers1, Jason C Morris, Kathryn E Fairfull-Smith

  • 1ARC Centre of Excellence for Free Radical Chemistry and Biotechnology, Faculty of Science and Engineering, Queensland University of Technology, 2 George St, Brisbane, QLD 4001, Australia. s.bottle@qut.edu.

Chemical Communications (Cambridge, England)
|September 28, 2013
PubMed
Summary

Methoxyamine is an ideal protecting group for nitroxides, easily introduced and removed under mild conditions. This method offers high yields for protecting and deprotecting functionalized nitroxides.

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Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups
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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
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Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups
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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
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Area of Science:

  • Organic Chemistry
  • Protecting Group Chemistry

Background:

  • Nitroxide moieties are important functional groups in various chemical applications.
  • Effective protecting groups are crucial for selective manipulation of complex molecules.

Purpose of the Study:

  • To introduce and evaluate the methoxyamine group as a novel protecting group for nitroxides.
  • To develop efficient methods for both the introduction and removal of the methoxyamine protecting group.

Main Methods:

  • Introduction of the methoxyamine group using iron(II) sulfate heptahydrate (FeSO4·7H2O) and hydrogen peroxide (H2O2) in dimethyl sulfoxide (DMSO).
  • Removal of the methoxyamine group via a Cope-type elimination using meta-chloroperoxybenzoic acid (mCPBA) under mild conditions.

Main Results:

  • The methoxyamine group was successfully introduced to functionalized nitroxides with high yields (>90%).
  • The methoxyamine group was efficiently removed under mild conditions, yielding 70-90% of the deprotected nitroxide.
  • The protection/deprotection strategy proved to be selective and high-yielding.

Conclusions:

  • The methoxyamine group is a highly effective and versatile protecting group for nitroxides.
  • The developed synthetic route offers a robust and efficient method for nitroxide chemistry.