Abstract
The presence of nitroso oxide intermediates has been studied in the photooxidation of phenyl azide. The hydroxylation of benzenes occurred and was accelerated by electron-donating groups. Sulfides were oxidized to sulfoxides, but the oxygenation and deoxygenation of sulfoxides proceeded concurrently; these reactions were facilitated by electron-donating substituents. Trapping of the intermediates by added nitrosobenzenes was most efficient, approaching 80% O transfer. The relative reactivity order (styrenes, PhN=O>>Ph 2 S>Ph 2 SO>PhH), substituent effects, and the stereochemistry of hydroxylation of C-H bonds characterized the electrophilic radical nature of nitroso oxides. An 18 O-tracer study revealed that a unimolecular isomerization of nitroso oxides to nitro compounds proceeds competitively with the O transfers; The reactivity of XOO species is discussed on the basis of electronegativity of X
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