43020-14-0Relevant articles and documents
Pd(II)-catalyzed sequential C-C/C-O bond formations: A new strategy to construct trisubstituted furans
Zheng, Meifang,Huang, Liangbin,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 1838 - 1841 (2013/06/04)
Palladium-catalyzed oxidative difunctionalization of enol ethers with 1,3-dicarbonyl compounds to construct trisubstituted furans in one step under mild conditions is described. The reaction is thought to proceed through a C-C bond formation along with a C-O bond closing the ring structure. Oxygen is the sole oxidant regenerating the Pd(II) catalyst.
Synthesis of 2,3,5-Trisubstituted Furans by the Acid-Catalyzed Decomposition of 1,2-Dioxan-3-ols
Qian, Chang-Yi,Hirose, Jun-ichi,Nishino, Hiroshi,Kurosawa, Kazu
, p. 1219 - 1228 (2007/10/02)
Thirteen new 2,3,5-trisubstituted furans were prepared by the acid-catalyzed decomposition of 6,6-disubstituted 1,2-dioxan-3-ols in 57-93percent yields.The reaction could be accounted for as the consequence of an oxygen-oxygen bond cleavage by acid and the migration of a phenyl group at the C-6 position followed by cyclization and elimination of a phenol.The migratory aptitude was in the order of 4-MeOC6H4- greater than 4-MeO6H4- greater than Ph- = 4-FC6H4- greater than 4-ClC6H4- = 4-BrC6H4- that was found from the competitive phenyl migration in the reaction of 1,2-dioxan-3-ols bearing two different substituents at the C-6 position.