Journal
STRUCTURAL CHEMISTRY
Volume 23, Issue 2, Pages 441-449Publisher
SPRINGER/PLENUM PUBLISHERS
DOI: 10.1007/s11224-011-9887-8
Keywords
1,2,4,5-Tetraoxane; X-ray analysis; Intermolecular interaction; Photolysis; Thermolysis
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The crystal structures of valerophenone diperoxides trans-1 and cis-1 were elucidated by X-ray crystallographic analysis. The 1,2,4,5-tetraoxane rings of both compounds adopt chair conformations. Intermolecular CH center dot center dot center dot O hydrogen bond, pi-pi, and CH/pi interactions exist in cis-1, whereas only CH/pi interactions exist in trans-1. In the asymmetric unit of the crystal, a half molecule exists for trans-1, while one molecule for cis-1 which shows whole-molecule disorder. Solid-state photolysis (at 254 nm) or solution-state thermolysis (at 150 A degrees C) of trans-1 and cis-1 produced valerophenone (2) and butyl benzoate (3). Rationalization of the solid-state photoreactivity of the diperoxides by their crystal structures was attempted.
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