| Abstract: | Heterocyclic three-membered rings with an exocyclic double bond merit special interest in view of their ring strain and their fascinating chemistry. Their synthesis, thermal decomposition, ring opening, and cycloaddition reactions will be discussed in this review. α-Lactams, alkylideneaziridines, diaziridinones, and diaziridinimines belong to the best known classes, but the chemistry of alkylideneoxiranes and -thiiranes, α-lactones, α-thiolactones, thiiranimines, and aziridinimines has also been studied to some extent. Two elusive three-membered rings are oxiranimines and thiaziridinimines; the former were postulated as reactive intermediates in the thermal decomposition of α-lactams, whereas the latter were trapped efficiently with double and triple bonds during thermolysis of N-sulfonyliminothiatriazolines. In spite of many attempts to prepare thione derivatives of the title compounds, they are still unknown. Included in this review are also some open-chain dipolar species which are isomeric with the heterocyclic three-membered rings. |
