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Review | Regular issue | Vol 20, No. 6, 1983, pp.1127-1171
Published online, 1st January, 1970
DOI: 10.3987/R-1983-06-1127
Cycloaddition, Ring-opening, and Other Novel Reactions of Thiophenes

Brian Iddon

*Department of Chemistry and Applied Chemistry, The Ramage Laboratories, University of Salford, Salford M5 4WT, U.K.


Synthetically useful reactions of thiophenes and benzo[b]thiophenes are reviewed in which the aromaticity of the thiophene ring is lost either permanently or temporarily, i.e. so-called “non-benzenoid” reactions. These include cycloadition reactions with arynes, hetarynes, carbenes, nitrenes, olefins, acetylenes, ketones, and other substrates and various ring-opening reactions, e.g. of organometallic derivatives and 2-aminothiophenes. Also reviewed are C-2 protonation and reactions of thiophenes at the sulphur atom, e.g. alkylation. Brief reference is made to thiophene l,l-dioxides and attention is drawn to other little-used reactions of thiophenes of potential synthetic usefulness, e.g. inverted reactivity of thienyl-lithium compounds.