88343-92-4Relevant academic research and scientific papers
Copper-Catalyzed 1,6-Hydrodifluoroacetylation of para-Quinone Methides at Ambient Temperature with Bis(pinacolato)diboron as Reductant
Ke, Miaolin,Song, Qiuling
supporting information, p. 384 - 389 (2017/02/10)
An original and efficient copper-catalyzed 1,6-hydrodifluoroacetylation of para-quinone methides with difluoroalkyl bromides has been described with bis(pinacolato)diboron (B2pin2) as reductant. In this reaction, a new C(sp3)–CF2bond is constructed under smart conditions. A broad substrate scope of para-quinone methides (p-QMs) make this protocol very practical and attractive. Preliminary mechanistic studies manifested that a difluoroalkyl radical pathway was involved in this reaction. Also the presence of the diboron reagent was an essential requisite in this transformation. (Figure presented.).
Oxygen Transfer fom Oxaziridines: A Chemical Model for Flavin-Dependent Monooxygenases
Wagner, William R.,Spero, Denice M.,Rastetter, William H.
, p. 1476 - 1480 (2007/10/02)
The ability of several aryloxaziridines to transfer an oxygen atom to phenolates was examined. 2-(p-Nitrophenyl)-3-tert-butyloxaziridine (1) was found to oxidize potassium 2,6-dialkylphenolates to the corresponding p-benzoquinones.Product studies and an observed ESR signal suggest an electron-transfer mechanism for these oxidations. 18O-labeled oxaziridine 30 was prepared.Oxidations of phenolates with 30 rigorously establish the oxaziridine ring oxygen as the atom that is transferred to substrate.Kinetic studies with oxaziridine 1 and the isomeric nitrone 15 rule out the nitrone as an obligate intermediate in the oxygen-transfer reaction.In the oxidation of substrate, a single electron transfer from phenolate to oxaziridine is thought to generate a phenoxy/nitroxyl radical pair, which upon coupling and fragmentation achieves the oxygen transfer.These oxygen-transfer reactions serve as models for the proposed flavin-based oxaziridine 34 in enzyme-mediated monooxygenations.
