Dearomatization of furans via [2,3]-Still-Wittig rearrangement
Furans and benzofurans of type 1 were dearomatized via the [2,3]-Still-Wittig rearrangement. Enol ethers 2 could be isolated or isomerized to the corresponding furans 3. The substitution pattern at the homofuranylic position had a strong influence on reaction behavior. Benzofurans rearranged with the greatest efficiency, and employment of a 3-substituted benzofuran (1; R′=CH3) allowed the creation of a quaternary carbon center.
Caruana, Patrick A.,Frontier, Alison J.
p. 10921 - 10926
(2007/10/03)
A New Preparation of Benzofurans Utilizing Trimethylsilyldiazomethane
o-Triisopropylsiloxyaryl ketones and aldehydes smoothly reacted with the lithium salt of trimethylsilyldiazomethane to give o-triisopropylsiloxyphenylacetylenes which were easily converted to benzofurans by treatment with tetra-n-butylammonium fluoride. 3-Benzofuranmethanols were also obtained when the reaction was conducted in the presence of carbonyl compounds.
Ito, Yasuko,Aoyama, Toyohiko,Shioiri, Takayuki
p. 1163 - 1164
(2007/10/03)
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