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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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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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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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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.
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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.
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Metal-Free Synthesis of 1,3-Divinylimidazolidin-2-One.

Sabine Lorenzen1, Roland Graf1, Nikolai V Ignat'ev1,2

  • 1Institute of Inorganic Chemistry, Institute for Sustainable Chemistry & Catalysis with Boron (ICB), University of Würzburg, Würzburg, Germany.

Chemistryopen
|March 6, 2026
PubMed
Summary

A novel one-pot synthesis for 1,3-divinylimidazolidin-2-one (DVI) was developed using readily available starting materials. This efficient method yields high-purity DVI without catalysts, offering a greener alternative with carbon dioxide utilization.

Keywords:
aminesstructure elucidationvinyl compoundsvinyl nitrogen compounds dehydrochlorination

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Green Chemistry

Background:

  • 1,3-divinylimidazolidin-2-one (DVI) is a valuable chemical intermediate.
  • Existing synthesis methods may involve complex procedures or expensive reagents.

Purpose of the Study:

  • To develop a novel, efficient, and cost-effective one-pot synthesis for 1,3-divinylimidazolidin-2-one (DVI).
  • To explore alternative sustainable routes for DVI preparation.

Main Methods:

  • A two-step one-pot synthesis utilizing di(chloroethyl)amine and phosgene or triphosgene.
  • Assessment of an alternative synthetic route employing carbon dioxide.

Main Results:

  • High purity and good yield of DVI were achieved.
  • The synthesis was accomplished without the need for any catalytic system.
  • An alternative route using carbon dioxide was successfully evaluated.

Conclusions:

  • The developed one-pot synthesis offers a convenient and efficient method for producing DVI.
  • The process is cost-effective due to the use of inexpensive starting materials.
  • The exploration of carbon dioxide as a reagent highlights a potential for greener DVI production.