1994
DOI: 10.1021/ja00092a019
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Thermolysis of 3,3-Bis(phenylmethyl)-1,2-dioxetane: Radical-Induced Formation of the Unusual Decomposition Product 3-Phenyl-1-(phenylmethoxy)-2-propanone

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Cited by 11 publications
(11 citation statements)
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“…The hydroxymethyl radical, which is generated in the photolysis of 1-hydroxy-3-phenyl-2-propanone along with the phenylmethyl radical (after decarbonylation), shows a moderate tendency to oxidize dGuo (50% conversion of dGuo). The low reactivity of the phenylmethyl radicals was independently confirmed by the rather ineffective oxidation of dGuo (4% conversion of dGuo compared to 40% for HTMD) when 3,3-bis(phenylmethyl)-1,2-dioxetane (DBD, 20 mM) was employed as efficient thermal source of such species …”
Section: Resultssupporting
confidence: 77%
See 1 more Smart Citation
“…The hydroxymethyl radical, which is generated in the photolysis of 1-hydroxy-3-phenyl-2-propanone along with the phenylmethyl radical (after decarbonylation), shows a moderate tendency to oxidize dGuo (50% conversion of dGuo). The low reactivity of the phenylmethyl radicals was independently confirmed by the rather ineffective oxidation of dGuo (4% conversion of dGuo compared to 40% for HTMD) when 3,3-bis(phenylmethyl)-1,2-dioxetane (DBD, 20 mM) was employed as efficient thermal source of such species …”
Section: Resultssupporting
confidence: 77%
“…To assess the nature of the oxidizing species derived from the dioxetanes 1 α/ 1 β, 2 , and HTMD upon thermolysis, the inhibitory effect of a number of additives was tested in the dioxetane-mediated photooxidation of dGuo (Table ) and compared to photoexcited benzophenone (BP) triplets. DMPO, cresol,55a and galvinoxyl 55a were representatively examined as well-established radical scavengers. Such radical scavengers do not only intercept radicals, but also influence the triplet-excited states.…”
Section: Resultsmentioning
confidence: 99%
“…It is usually assumed , that dioxetane decomposition takes place via biradical intermediates • OCH 2 −CH 2 O • formed after initial cleavage of the O−O bond. Due to the weak interaction between the two radical centers, especially in the anti conformation, such a biradical is electronically rather complex since there is a possible 8-fold (4-fold triplet and 4-fold singlet) state quasi-degeneracy.…”
Section: Theoretical Background and Computational Detailsmentioning
confidence: 99%
“…• Finally, for the formation of 3-Cu from 1-Cu c -2 or 4-Cu from 1-Cu t -2 , a stepwise mechanism can be suggested in which an O–O bond cleavage of incorporated 1,2-dioxetane leads initially to the 1,4-dioxyl diradical. Subsequently, a β-cleavage of C(11)–C α ( 1-Cu c -2 ) or C(16)–C α ( 1-Cu t -2 ) bonds afforded two carbonyl fragments.…”
Section: Resultsmentioning
confidence: 99%