57732-89-5Relevant academic research and scientific papers
Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis
Rivero, Alexandra R.,Fodran, Peter,Ondrejková, Alica,Wallentin, Carl-Johan
supporting information, p. 8436 - 8440 (2020/11/03)
A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1°, 2°, and 3° alcohols and allows their use in the functionalization of C(sp3)-H and C(sp2)-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.
Ketene. Part 23. Conformational Control of the Addition Reactions of Ketenes with N-Phenylnitrones
Falshaw, Christopher P.,Hashi, Nur A.,Taylor, Giles A.
, p. 1837 - 1844 (2007/10/02)
X-Ray analysis shows that the nitrone group in (5a) is not distorted, disproving a previous explanation for the formation of oxazolidinones rather than indolones in the reactions with ketenes.Nitrone (5c) reacts with dimethylketene and diphenylketene to form oxazolidinones (6c,d) whereas nitrones (5d) and (5e) under similar conditions form indolone derivatives (9).Oxazolidinone formation by the reaction of ketenes with nitrones (5a-c) results from restricted rotation about the N-phenyl bond preventing the -migration (3) -> (4), which precedes indolone formation.
