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Generation of N,N-Di(4-bromophenyl)nitrenium Ion under Acidic Conditions: Search for a Nitrenium Dication

Andrea N Zeppuhar1, Daniel E Falvey1

  • 1Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742 United States.

The Journal of Organic Chemistry
|June 27, 2020
PubMed

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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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