The reaction of trans-1,2-bis(4-methoxyphenyl)cyclohexane-1,2-diol with excess amounts (4 eq.) of tris(2,4-dibromophenyl)aminium hexachloro-antimonate affords only 1,6-bis(4-methoxyphenyl) hexane-1,6-dione through an oxidative cleavage. An analogous reaction of the corresponding cis-diol, gives mainly 2,2-bis(4-methoxyphenyl)cyclohexanone, whose formation might proceed through an oxidative rearrangement alternative, at least in part, to the classic acid catalysed pinacol rearrangement.
Insights into Pinacol Rearrangement: Oxidative versus Acid-Catalyzed Mechanism
Casiello M;Fusco C;D'Accolti L;Nacci A
2021
Abstract
The reaction of trans-1,2-bis(4-methoxyphenyl)cyclohexane-1,2-diol with excess amounts (4 eq.) of tris(2,4-dibromophenyl)aminium hexachloro-antimonate affords only 1,6-bis(4-methoxyphenyl) hexane-1,6-dione through an oxidative cleavage. An analogous reaction of the corresponding cis-diol, gives mainly 2,2-bis(4-methoxyphenyl)cyclohexanone, whose formation might proceed through an oxidative rearrangement alternative, at least in part, to the classic acid catalysed pinacol rearrangement.File in questo prodotto:
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Descrizione: Insights into Pinacol Rearrangement: Oxidative versus Acid-Catalyzed Mechanism
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