ol0165995_si_001.pdf (154.28 kB)
An Unexpected Paternò-B chi Reaction in the Crystalline State
journal contribution
posted on 2001-09-28, 00:00 authored by Ting Kang, John R. SchefferThe 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.