56795-82-5Relevant articles and documents
O-Heterocycles from Unsaturated Carbonyls and Dimethoxycarbene
Croisetière, Jean-Philippe,Spino, Claude
, p. 5609 - 5618 (2018/05/08)
The (4+1)-annulation of dimethoxycarbene with readily accessible α,β-unsaturated carbonyls gives cyclic orthoesters, which can then be converted in just a few steps to other O-heterocycles, including methoxyfurans, furanones, and furans.
Photosensitized Oxidation of Furans. Part 13. Trapping Reactions of the Carbonyl Oxides Obtained from Some 2-Methoxy-5-phenylfurans
Graziano, M. Liliana,Iesce, M. Rosaria,Cimminiello, Guido,Scarpati, Rachele
, p. 1699 - 1704 (2007/10/02)
The dye-sensitized photo-oxygenation in methanol of the 2-methoxy-5-phenylfurans (1a-c), unsubstituted at C-4 with electron-withdrawing groups, leads to the hemiperacetals (4a-c).The reaction provides the first incontrovertible evidence for carbonyl oxide
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.