A study was conducted to perform mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-Quinone methide (QM). The study focused on mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-Quinone methide, as led to the formation of chromenes. Vinyl o-QM was prepared through oxidation of phenol 3, while the E configuration of the exo-alkylidene bond was established by detailed nuclear magnetic resonance (NMR) studies and X-ray crystallography. The structure of the dimer was also confirmed by X-ray crystallography. Kinetic investigation of the uncatalyzed cyclization of Vinyl o-QM and chromene revealed the sensitivity of the rate of the reaction to light, oxygen, and adventitious acid, studying the reactivity of o-QM.
- Activation parameters
- Density functional calculations
ASJC Scopus subject areas
- Organic Chemistry