96747-12-5Relevant articles and documents
Organocatalytic Nitroaldol Reaction Associated with Deuterium-Labeling
Yamada, Tsuyoshi,Kuwata, Marina,Takakura, Ryoya,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 637 - 641 (2017/12/13)
A deuterium-labeling reaction of nitroalkanes in deuterium oxide and the subsequent nitroaldol reaction have been accomplished under basic and organocatalytic conditions to provide the deuterium-labeled β-nitroalcohols in high yields and high deuterium contents. β-Deuterated β-nitroalcohols could be smoothly obtained from the reaction of nitroalkanes and various electrophiles using the easily-removal basic resin WA30. Furthermore, the asymmetric nitroaldol reaction using nitromethane and α-keto esters as electrophiles in the presence of a quinine-derived organocatalyst in deuterium oxide could provide the desired β-deuterated nitroalcohol derivatives with high enantioselectivities. (Figure presented.).
Photochemical Reactions of Mercapto/Amino Substituted Alkyl Phenylglyoxylates Induced by Intramolecular Electron Transfer
Hu, Shengkui,Neckers, Douglas C.
, p. 2751 - 2766 (2007/10/03)
2'-Alyothio ethyl phenylglyoxylates (1) and 2'-dimethylamino ethyl phenylglyoxylate (10) were synthesized and their photochemistry studied.In contrast to their oxygen analog 3, which give normal Norrish type II cleavage products, the title compounds undergo intermolecular electron transfer from the heteroatom (sulfur/nitrogen) to the excited carbonyl group, followed by proton transfer and subsequent closing of the resulting biradical to produce seven-mebered (11) lactones in high yield.Thiadialkyl phenylglyoxylates (9) react inefficiently due to intramolecular self-quenching of phenylgluoxylate chromophores.The photoreactivity of α-oxothioester (14) was compared with that of its nitrogen (α-oxoamide) and oxygen (phenylglyoxylate) counterparts. - Keywords: Photochemical; Mercapto; Amino; Phenylglyoxylates; Electron Transfer