106552-33-4Relevant articles and documents
Direct Photolysis and Electron Transfer Photooxygenation of Enol Acetates of 3-Phenylpropiophenones
Algarra, Felipe,Baldovi, Maria V.,Garcia, Hermenegildo,Miranda, Miguel A.,Primo, Jaime
, p. 209 - 216 (2007/10/02)
Direct photolysis of enol acetates of 3-phenylpropiophenones 1a-c gives rise to the parent propiophenones 2a-c and the 1,3-acyl shift products 3a-c.By contrast, 2,4,6-triphenylpyrylium tetrafluoroborate sensitized photolysis of substrates 1a-c affords the α-acetyloxypropiophenones 7a-c as the most general products.These results have been rationalized according to the generation of radical pairs in the direct photolysis and radical cations in the photoinduced electron transfer processes. Keywords.Enol acetates of 3-phenylpropiophenones; 1,3-Acyl migration; Photoinduced electron transfer; 2,4,6-triphenylpyrylium tetrafluoroborate.
A Facile One-Pot Synthesis of Vicinal Di- and Triketones from α-Methylene Ketones by NBS-DMSO Oxidation
Tatsugi, Jiro,Izawa, Yasuji
, p. 2747 - 2763 (2007/10/02)
The reaction of 1,2-diarylethanones (1a-u) with N-bromosuccinimide in anhydrous dimethyl sulphoxide afforded diarylethanediones (2a-u) in excellent yields.Under similar conditions, 1-phenyl-2-butanone (3) gave 1-phenyl-1,2-butanedione (4) in fair yield in addition to a small amount of 1-phenyl-3-methylthio-1,2-butanedione (5) and 1-phenyl-1-methylthio-2-butanone (6). 4-Phenyl-2-butanone (7), 1,3-diphenyl-2-propanone (9), and 1,3-diphenyl-1,3-propanedione (10) gave the corresponding triketones monohydrate (8) and (11). 1-Indanone (12), 2-indanone (13), and 1,3-indandione (14) gave ninhydrin (15) in good yields.In the case of 3-phenyl-1-indanone (16), 3-phenyl-2-bromo-1-indanone (17), 3-phenyl-2-bromo-1-indenone (18) and 3-phenyl-1-indenone (19) were obtained. 1-Phenyl-1-propanone (20) and 1-phenyl-1-butanone (22) gave the corresponding α-(methylthio)ketones (21) and (22). 1,3,3-Triphenylpropanone (24a) and 1-phenyl-3-methyl-1-butanone (24b) yielded only the corresponding α-bromoketones (25a,b) in good yields.These α-bromoketones, however, afforded the corresponding α-diketones (26a,b) in moderate yields when α-bromoketones reacted with dimethyl sulphoxide in the presence of AgBF4.