Journal of Organic Chemistry p. 4237 - 4244 (1984)
Update date:2022-08-04
Topics:
Hassner, Alfred
Fibiger, Richard
Andisik, Donald
Hydrazoic acid, though unreactive to alkenes, adds readily to enol ethers.In the presence of Lewis acids, in particular TiCl4, addition takes place readily to phenylethylenes or 1,1-disubstituted ethylenes to produce alkyl azides.Regiochemical, electronic, and steric influences were explored.TiCl4 also served to catalyze conversion of benzyl or tertiary alcohols to azides.Monosubstituted alkenes or primary alcohols are not affected.
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