Alcohol-alkyl azide reaction, intermolecular

Pearson and coworkers also developed intermolecular reactions of azides with carboca-tions. Thus, benzylic or tertiary alcohols, when treated with alkyl azides in the presence of SnCLt or TfOH followed by NaBH4-mediated reduction, provided tertiary or secondary amines. Both cyclic and acyclic alcohols were compatible with these reactions, though mixtures of constitutionally isomeric products often resulted (Scheme 7.23). 

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