2:1 Adducts Arising from Reactions between Benzynes and 1,3,4-Oxadiazoles

Alexander L. Guzman, Paul V. Kevorkian, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review


2:1 adducts arise from the reaction of 2,5-diaryl-1,3,4-oxadiazoles and benzynes generated from the hexadehydro-Diels-Alder (HDDA) reaction. Density functional theory computations support a mechanistic manifold that includes a concerted SNAr process. Additionally, the benzyne trapping reaction of 2,5-dimethyl-1,3,4-oxadiazole affords an unusual acylimine-containing 2:1 adduct, which is the first case in which a dearomatized product has arisen from a HDDA reaction.

Original languageEnglish (US)
Pages (from-to)3834-3839
Number of pages6
JournalOrganic Letters
Issue number18
StatePublished - May 10 2024

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© 2024 American Chemical Society.

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  • Journal Article


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