ArticleAngewandte Chemie (International ed. in English)2022
Electronic Character of α,3-Dehydrotoluene Intermediates Generated from Isolable Allenyne-Containing Substrates.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5 citing papers in PubMed.
- Utilizing the Pentadehydro-Diels-Alder Reaction for Polycyclic Aromatic Compound Synthesis: Diels-Alder-Based Linker Transformation.Molecules (Basel, Switzerland) · 2025Article
- Free carbenes from complementarily paired alkynes.Nature chemistry · 2024Article
- Cascade reactions of HDDA-benzynes with tethered cyclohexadienones: strain-driven events originating fromChemical science · 2024Article
- A Distinct Mode of Strain-Driven Cyclic Allene Reactivity: Group Migration to the Central Allene Carbon Atom.Journal of the American Chemical Society · 2023Article
- Electronic Character of α,3-Dehydrotoluene Intermediates Generated from Isolable Allenyne-Containing Substrates.Angewandte Chemie (International ed. in English) · 2022Article
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2 authors.
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Abstract
We report here the generation of α,3-dehydrotoluenes, a relatively rare subset of reactive intermediates of the dehydroaromatic family, from isolable allenynes. The substructure motif in the allenyne substrates is distinct from, and complementary to, those found in Myers-Saito/Schmittel-type cycloisomerizations. The reactions reported here give rise to product profiles that provide insight about the electronic nature (i.e., diradical vs. zwitterion vs. cyclic allene) of the particular isomeric DHT(s) that is(are) produced under different reaction conditions differing most significantly in the polarity of the reaction solvent. One example also revealed previously unobserved carbene-like reactivity of the DHT.
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