Skeletal Modification of 1,2-Benzoquinone Monoximes into Conjugated ( Z , Z )-Dienes and 2-Cyanocyclopentadienones by Ring-Opening and Ring Contraction
Abstract
A new strategy for stepwise dearomative functionalization of catechols is presented. The key substrates, 1,2-benzoquinone monoximes derived from readily available catechols, could be converted to conjugated ( Z, Z )-dienes and 2-cyanocyclopentadienones. This divergent synthesis was enabled through either trapping the acylium intermediates, which were generated by C–C bond cleavage of 1,2-benzoquinone monoximes, with nucleophiles or a subsequent intramolecular Friedel–Crafts acylation. Further transformations of previously unknown dearomatized products were then delineated.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Oxidative Organic Chemistry Reactions
Asymmetric Synthesis and Catalysis
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 9
- Pages
- 3572–3577
- Publication date
- 23 February 2026
- Language
- EN