Related Experiment Videos
An unexpected Paternò-Büchi reaction in the crystalline state
1Department of Chemistry, University of British Columbia, 2036 Main Mall, Vanouver, British Columbia, Canada V6T 1Z1.
Organic Letters
|October 12, 2001
Abstract:
[reaction: see text]. The solution and solid-state photochemistry of a series of aryl 1-phenylcyclopentyl ketones (1) was investigated. While typical Norrish type I products were formed in solution, irradiation of crystals of 1 afforded the novel oxetanes 3 and 4 regiospecifically. The formation of the oxetanes is believed to occur through Norrish type I cleavage and hydrogen abstraction, producing an alkene and an aldehyde, followed by a Paternò-Büchi reaction within the crystal lattice cage.