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Review | Regular issue | Vol 92, No. 5, 2016, pp.793-828
Published online, 11th March, 2016
DOI: 10.3987/REV-16-837
Ring-Substitution, Enlargement, and Contraction by Base-Induced Rearrangements of N-Heterocyclic Ammonium Salts

Eiji Tayama*

*Department of Chemistry, Faculty of Sciences, Niigata University, Ikarasi 2-8050, Niigata 950-2181, Japan


An overview of the utility of base-induced Stevens, Sommelet–Hauser, and related sigmatropic rearrangements of N-heterocyclic ammonium salts into various types of N-heterocycles reported after 1970 will be described. The synthetic transformations are classified as N-heterocyclic ring-substitution, ring-enlargement, and ring-contraction.