Collect. Czech. Chem. Commun. 1999, 64, 2007-2018

Temperature Dependent Solvent Effects in Photochemistry of 1-Phenylpentan-1-ones

Petr Klán* and Jaromír Literák

Department of Organic Chemistry, Masaryk University, Kotlářská 2, 611 37 Brno, Czech Republic


Temperature dependent solvent effects have been investigated on the Norrish Type II reaction of 1-phenylpentan-1-one and its p-methyl derivative. Efficiencies of the photoreaction were studied in terms of solvent polarity and base addition as a function of temperature. Such a small structure change as the p-methyl substitution in 1-phenylpentan-1-one altered the temperature dependent photoreactivity in presence of weak bases. The experimental results suggest that the hydrogen bonding between the Type II biradical intermediate OH group and the solvent is weaker for 1-(4-methylphenyl)pentan-1-one than that for 1-phenylpentan-1-one at 20 °C but the interactions probably vanish in both cases at 80 °C.

Keywords: Photochemistry; Solvent effects; Ketones; Norrish Type II reaction; Valerophenone.