An unexpected Paternò-Büchi reaction in the crystalline state.
[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.
Kang
T
T
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vanouver, British Columbia, Canada V6T 1Z1.
Scheffer
J R
JR