jo0266238_si_001.pdf (269.75 kB)
Mechanistic Significance of Perepoxide Trapping Experiments, with Epoxide Detection, in 1Δg Dioxygen Reactions with Alkenes
journal contribution
posted on 2003-03-11, 00:00 authored by Andrea Maranzana, Giovanni Ghigo, Glauco TonachiniThe reactions of 1O2 with alkenes can share open-chain diradicals or cyclic peroxiranes as common
polar intermediates. The latter in particular has been postulated on the basis of trapping
experiments, which exploit the capability of reducing agents (R) to extract an oxygen atom from
the putative perepoxide, to generate an epoxide. This theoretical study illustrates that trapping
experiments cannot distinguish between a peroxirane and an open-chain intermediate pathway,
because an epoxide is the shared outcome of the attack by R.