26431-43-6Relevant articles and documents
Asymmetric Synthesis of Benzoin by SmI2-Mediated Enantioselective Protonation
Takeuchi, Seiji,Miyoshi, Norikazu,Hirata, Kenji,Hayashida, Haruyoshi,Ohgo, Yoshiaki
, p. 2001 - 2003 (1992)
Samarium (Z)-1,2-diphenylethen-1,2-diolate, which is considered to be an intermediate of a SmI2-mediated reduction of benzil, was protonated enantioselectively by quinidine to afford (R)-benzoin in 91 percentee.It was found that quenching the unreacted en
Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification
Zaghi, Anna,Ragno, Daniele,Di Carmine, Graziano,De Risi, Carmela,Bortolini, Olga,Giovannini, Pier Paolo,Fantin, Giancarlo,Massi, Alessandro
, p. 2719 - 2730 (2017/01/09)
A convenient heterogeneous continuous-flow procedure for the polarity reversal of aromatic α-diketones is presented. Propaedeutic batch experiments have been initially performed to select the optimal supported base capable to initiate the two electron-tra
Modification of the photochemical reactivity of α,β-diacetoxystilbene by adsorption onto a Fe3+-doped sepiolite: Comparison with the direct and 2,4,6-triphenylpyrylium-sensitized photolyses
Baldovi,Garcia,Miranda,Primo,Soto,Vargas
, p. 8113 - 8120 (2007/10/02)
Photolysis of α,β-diacetoxystilbene (1) adsorbed onto a Fe3+-doped sepiolite (Fe-Sp) leads to benzoic acid (3), 9,10-diacetoxyphenanthrene (5), diphenic anhydride (6), and benzil (7). While compounds 3, 5 and 6 are also observed in the direct irradiation of 1 in hexane solution, diketone 7 is formed under electron transfer conditions using 2,4,6-triphenylpyrylium tetrafluoroborate as photosensitizer. These results strongly suggest that formation of benzil (7) in the photolysis of 1 on Fe-Sp involves the intermediacy of 1+·, generated by single electron transfer from excited 1 to the iron active sites of the clay. In contrast to the unsubstituted stilbene, reactivity of 1+· with ground state molecular oxygen has been established by cyclic voltammetry through the current intensity decrease of the oxidation peak of 1 in the presence of oxygen. Finally, the thermodynamic feasibility of a direct electron transfer pathway between excited 1* and oxygen leading to the formation of a dioxetane intermediate is discussed.