Depto. Química Orgánica

AZIDES

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15/07/2017
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The azides can be obtained by nucleophilic substitution using sodium azide. This ion is a strong nucleophile while a weak base and therefore it easily leads to SN2 reactions, unless the reacting carbon is too crowded.
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If the azide attack is performed on an epoxide, the ring opening proceeds regioselectively following the cuasi-SN2 mechanism at the less hindered position.
Click here to go to epoxide ring-opening reactions.
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Azides yield amines by reduction. Therefore, the combined reaction of azide substitution and reduction allows one to get amines very conveniently.
One can also get ACYL-azides by an addition-elimination mechanism from acyl chlorides:
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Click here to go to the addition-elimination mechanism.
ACYLAZIDES decompose by heating following the so-called Curtius rearrangement, a reaction closely related to the Hofmann rearrangement of amides:
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