Decarbonylation Enables Chemodivergent Access to Guaiazulene-3-Oxalic and -Carboxylic Acid Derivatives.

Emma Audi, Carly M Zack, Esther M Ntankwa, William Blake Heston, Annika S Waples, Manana Tsiskarishvili, C Rose Kennedy, Shuming Chen, J Patrick Lutz

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Article in The Journal of organic chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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9 authors.

Emma AudiDepartment of Chemistry, St. Lawrence University, Canton, New York 13617, United States.

Carly M ZackDepartment of Chemistry, St. Lawrence University, Canton, New York 13617, United States.

Esther M NtankwaDepartment of Chemistry, St. Lawrence University, Canton, New York 13617, United States.

William Blake HestonDepartment of Chemistry, St. Lawrence University, Canton, New York 13617, United States.

Annika S WaplesDepartment of Chemistry and Biochemistry, Oberlin College, Oberlin, Ohio 44074, United States.

Manana TsiskarishviliDepartment of Chemistry, University of Rochester, Rochester, New York 14627, United States.

C Rose KennedyDepartment of Chemistry, University of Rochester, Rochester, New York 14627, United States.ORCID 0000-0003-3681-819X

Shuming ChenDepartment of Chemistry and Biochemistry, Oberlin College, Oberlin, Ohio 44074, United States.ORCID 0000-0003-1897-2249

J Patrick LutzDepartment of Chemistry, St. Lawrence University, Canton, New York 13617, United States.ORCID 0000-0002-5795-5049

Funding

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6 · The paper itself

Abstract

Guaiazulene derivatives are of interest due to the low cost of guaiazulene compared to azulene while still retaining many of the same unique electronic properties. Syntheses of guaiazulene-3-carboxylic acid and azulene-1-carboxylic acid derivatives have been described, but they typically rely on uncommon or toxic reagents such as oxalyl bromide or phosgene. We describe a new route to these compounds by functionalization with oxalyl chloride, followed by thermal or bromide-induced decarbonylation and quenching with a nucleophile. Combined experimental and computational studies suggest a concerted 1,2-halide shift mechanism for the decarbonylation.

Identifiers

PMID42329052

DOI10.1021/acs.joc.6c00848

PMCPMC13339644

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