Lewis Acid Catalyzed Conversion of Alkenes and Alcohols to Azides

Alfred Hassner, Richard Fibiger, Donald Andisik

Research output: Contribution to journalArticlepeer-review

76 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)4237-4244
Number of pages8
JournalJournal of Organic Chemistry
Volume49
Issue number22
DOIs
StatePublished - Jan 1984
Externally publishedYes

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