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

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

doi:10.1021/acs.orglett.4c01005

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

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

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 S_NAr 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 language	English (US)
Pages (from-to)	3834-3839
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.4c01005
State	Published - May 10 2024

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© 2024 American Chemical Society.

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abstract = "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.",

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AU - Guzman, Alexander L.

AU - Kevorkian, Paul V.

AU - Hoye, Thomas R.

PY - 2024/5/10

Y1 - 2024/5/10

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85192147982

UR - https://www.scopus.com/pages/publications/85192147982#tab=citedBy

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SN - 1523-7060

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SP - 3834

EP - 3839

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

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

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