13.21 Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?
13.21 Why cannot aromatic primary amines be prepared by Gabriel phthalimide synthesis?
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1 Answer
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Gabriel phthalimide synthesis is used for the preparation of aliphatic primary amines. It involves nucleophilic substitution (SN2) of alkyl halides by the anion formed by the phthalimide.But aryl halides do not undergo nucleophilic substitution with the anion formed by the phthalimide.
Therefore aromatic primary amines cannot be formed by gabriel phthalimide process.
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