Photoinduced deprotonation of cyclopentene oxide radical cations in low-temperature Freon matrices

Abstract

Upon the photolysis (λ = 546 nm) of X-ray irradiated cyclopentene oxide/Freon solutions at 77 K, irreversible proton abstraction in the ring-open form of the cyclopentene oxide radical cation occurs, affecting the bridgehead carbon. This affords unstable 6-oxabicyclo[3.1.0]hexan-1-yl radicals, which undergo rearrangement to form ring-open terminal C-centered alkyl radicals detected as final products.