A vinylogous Norrish reaction as a strategy for light-mediated ring expansion.

Evgueni Gorobets James W PapatzimasJorge DouradoGoonay YousefalizadehJinGyu LeeDuncan K Brownsey Kevin G Stamplecoskie Rebecca L Davis Darren J Derksen

Published in: Chemical communications (Cambridge, England) (2022)

The reactions of bicyclic divinyl ketones display wavelength-dependent changes in product formation. UV irradiation results in the formation of competitive [6,3,5] and [7,3,5] tricyclic unsaturated ketones that subsequently undergo ring expansion and reaction with a range of nucleophiles. DFT calculations and transient absorption experiments were completed that are consistent with a vinylogous Type II Norrish pathway.

Keyphrases

density functional theory
molecular dynamics
molecular dynamics simulations
molecular docking
electron transfer
radiation therapy
brain injury
blood brain barrier
monte carlo
crystal structure