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Topic: azocoupling  (Read 2748 times)

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Offline alexanderdundua

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azocoupling
« on: November 08, 2007, 07:27:37 AM »
Is it possible to caary out azo coupling reaction between arenediazonium salt and bromobenzene?
In organic chemistry books I could only find reactions between arenediazonium salts and phenol or aniline derivatives.

Offline shelanachium

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Re: azocoupling
« Reply #1 on: November 08, 2007, 09:10:04 AM »
No. The diazonium ion is a weak electrophile and will attack only electron-rich aromatic systems. The O and N atoms in phenols and anilines have pi-electrons that are partially donated to the aromatic nucleus, rendering it electron-rich and susceptible to attack by diazonium ions. Whilst Br has pi-electrons these are in much larger orbitals that overlap poorly with those of the benzene ring, and as Br is strongly electronegative it withdraws electrons from the benzene ring, deactivating it to attack by electrophiles.

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