Decarbonylation Enables Chemodivergent Access to Guaiazulene-3-Oxalic and -Carboxylic Acid Derivatives
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.
Repository Citation
Audi, Emma, Zack, Carly M., Ntankwa, Esther M., et al. 2026. "Decarbonylation Enables Chemodivergent Access to Guaiazulene-3-Oxalic and -Carboxylic Acid Derivatives." Journal of Organic Chemistry 91(26).
Publisher
American Chemical Society (ACS)
Publication Date
6-2026
Publication Title
Journal of Organic Chemistry
Department
Chemistry and Biochemistry
Document Type
Article
DOI
https://doi.org/10.1021/acs.joc.6c00848
Language
English
Format
text
