ArticleOrganic letters2019
Benzyne Cascade Reactions via Benzoxetenonium Ions and Their Rearrangements to o-Quinone Methides.
Article in Organic letters, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Thermal and Photochemical Reactions of Organosilicon Compounds.Molecules (Basel, Switzerland) · 2025Review
- Advances in the synthesis of nitrogen-containing heterocyclic compounds byRSC advances · 2023Review
- Article
- Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.Chemical reviews · 2021Review
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3 authors.
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Abstract
A new thermal isomerization of polyynes is described. Benzyne intermediates substituted by a C(RR')OR'' substituent adjacent to one of the benzyne sp-hybridized carbons give rise to products in which the OR' moiety has migrated to the proximal benzyne carbon. This process likely proceeds via sequential formation of multiple reactive intermediates: an initial thermally generated benzyne, a strained benzoxetenonium ion, and an o-quinone methide. As some examples demonstrate, the overall transformation can be quite efficient. The mechanism of this novel reaction is further supported by experiments and DFT calculations.
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