Reactions of Diazonium Salts

by James

Description: Treatment of diazonium salts with various reagents leads to formation of a new bond to the aromatic ring and loss of nitrogen (N2).
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Notes: See below for the full range of reagents that can be used; this reaction can be used to introduce Cl, Br, I, CN, OH, F, and H, which makes it very useful.

Examples:


2-examples

Notes: Reactions that involve Cu salts are sometimes called Sandmeyer reactions.

Mechanism: The mechanism of these reactions are somewhat complex and beyond the scope of a typical introductory course. The reactions of copper halides (Sandmeyer reactions) are thought to proceed through free-radical intermediates.

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{ 7 comments… read them below or add one }

Angela Goddard

In the reduction to benzene, should the reactant be H3PO2 instead of H2PO3? That is how I have seen it elsewhere.

Reply

James

Shoot. Fixed. Thanks!

Reply

Petr Menzel

Hi, in the Examples the example 4: Ph-N+N + H3PO2 —> “benzene”. Why in the reaction Ph-N+N + HPO —> is produced “phenol”? Its is ok the other reaction? Thx, P.

Reply

James

You mean H3O+ ?

Reply

Petr Menzel

No, I mean acid HPO.

Reply

Petr Menzel

Hi, is the carbon C, where is bonded -N+N, the same carbon where is bonded the X from the Description? Thx, P.

Reply

James

Yes, it should be!

Reply

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