78304-96-8Relevant academic research and scientific papers
Diethylene Glycol Serving as Ethyne Equivalent: A Sustainable Approach toward 2,3-Disubstituted Furan
Yu, Jin-Tao,Shi, Bo,Peng, Haibo,Sun, Song,Chu, Haoke,Jiang, Yan,Cheng, Jiang
, p. 3643 - 3645 (2015)
In the presence of tert-butyl peroxide (TBHP), the copper-catalyzed annulation of 1,3-dicarbonyl compound with diethylene glycol was developed leading to 2,3-disubstituted furan. Diethylene glycol serves as a cheap and environmentally friendly equivalent of ethyne, with the release of H2O and alcohol as clean wastes. The procedure involves a sequential O- and C- functionalization of β-ketoester by diethylene glycol.
ELECTROOXIDATION OF 2-ARYLFURANS
Janda, Miroslav,Srogl, Jan,Dvorakova, Hana,Dvorak, Dalimil,Stibor, Ivan
, p. 906 - 916 (2007/10/02)
Electrochemical methoxylation of 2-phenylfuran (I) and 2-(4-nitrophenyl)furan (VI) proceeded anomalously, affording 5-methoxy-2-phenylfuran (XI) and 5-methoxy-2-(4-nitrophenyl)furan (XIII), respectively. 2-Phenyl-5-methylfuran (II) and methyl-2-(2-methylphenyl)-3-furoate (VIII) behaved normally giving the respective 2,5-dimethoxy-2,5-dihydrofuran derivatives XII and XIV.The suggested ECNECB mechanism of the anomalous methoxylation was confirmed by methoxylation of compound II, in which the methyl group hinders the last CB step, and also of compound VIII in whichthe aromaticity is suppresed by forced deviation from planarity.Forced deviation from planarity was moreover studied also on 2-(4-methylphenyl)furan (III), 5-methyl-2-(2-methylphenyl)furan (IV) and 3,5-dimethyl-2-(2-methylphenyl)furan (V) as model compounds.For all the derivatives the INDO charges were calculated and correlated with the 1H- and 13C-NMR spectra.The experimental electronic spectra were correlated with the theoretical ones (INDO-S-CI).All results obtained confirm the suggested mechanism.
