Journal of Organic Chemistry p. 333 - 339 (1989)
Update date:2022-08-05
Topics:
Sander, Wolfram W.
The thermal and photochemical reactions of phenylcarbene and diphenylcarbene in oxygen-doped matrices have been investigated.The primary thermal adducts of free carbenes and O2 are carbonyl O-oxides, which are characterized by IR and UV spectroscopy.Most characteristic are intense O-O stretching modes in the IR (ν=900 cm1-) and ?-->?* transitions in the UV (λ=400 nm) spectra.The carbonyl O-oxides are very photolabile toward long-wavelength irradiation (500-630 nm) and either rearrange to dioxiranes or split off oxygen atoms.The distribution of photoproductsis determined by substituents: benzophenone O-oxide mainly gives diphenyldioxirane while benzaldehyde O-oxide gives the aldehyde and oxygen atoms.The strong chemiluminescence observed during the thermal reaction is explained by the reaction of free carbenes and oxygen atoms forming a C=O bond in situ.This reaction is highly exothermic and produces carbonyl compounds in their triplet states.
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