52786-29-5Relevant articles and documents
Polarity reversal induced by electrochemically generated thiazol-2-ylidenes: The Stetter reaction
Orsini, Monica,Chiarotto, Isabella,Sotgiu, Giovanni,Inesi, Achille
experimental part, p. 3511 - 3517 (2010/07/09)
The inversion of the normal reactivity (umpolung) of aldehydes has been induced via N-heterocyclic carbenes (NHCs) thiazol-2-ylidenes 2a or 3a, generated by simple electrolyses of solutions containing thiazolium salt 2 or 3. Accordingly, 1,4-dicarbonyl compounds have been obtained, in mild conditions and in moderate to very high yields, via 1,4-addition of the Breslow intermediates to the suitable Michael acceptor. The procedure has been performed in classical organic solvents (VOCs) as well as in room temperature ionic liquids (RTILs). The different reactivity of aliphatic aldehydes vs the one of aromatic and heteroaromatic aldehydes has been emphasized.
Highly selective synthesis of 1-phenylpentane-1, 4-diones, and (E)-5-hydroxy-5-phenylpent-3-en-2-ones catalyzed by organophosphorus compounds
Zhang, Qing,Qiao, Yan-Fei,Huang, Min,Liang, Hong-Dong,Zhou, Ru-Jin
experimental part, p. 425 - 430 (2010/07/16)
1-Phenylpentane-1, 4-diones, and (E)- 5-hydroxy-5-phenylpent-3-en-2-ones were synthesized via organophosphine-catalyzed addition reaction of but-3-en-2-one with aldehydes. The features of the present protocols include high selectivity, operational simplicity, atom economy, and mild reaction conditions without transition metals.
Oxidative Generation of α-Radicals of Carbonyl Compounds from the α-Stannyl Derivatives and Their Reactions with Electron-Rich Olefins
Kohno, Yasushi,Narasaka, Koichi
, p. 322 - 329 (2007/10/02)
The oxidation of α-tributylstannyl alkanoates with tetrabutylammonium hexanitratocerate(IV) generates α-radicals of the alkanoates by eliminating the stannylium ion.The thus-formed radicals react with various electron-rich olefinic compounds, such as silyl enol ethers, giving addition products in good yield.This method formally achieves selective cross coupling between alkanoates and ketones.