- Photosensitized Oxidation of Furans. Part 12. Solvent Effects in Thermal Rearrangement of the 2,5-Peroxides of 2,5-Unsubstituted Furans
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The formation, thermal stability, and modes of thermal rearrangement of the 2,5-peroxides (1a-i) of 2,5-unsubstituted furans are reported.In apolar solvents the main product of thermal rearrangement is the cis diepoxide (3) accompanied by the epoxyfuranones (6) and (7).These rearrangements are thought to proceed via concerted processes, although no distinction can be made between them and rearrangements via diradicals.In basic solvents the 5-hydroxyfuran-2(5H)-ones (4) and (5) are isolated in high yields.In this case the rearrangements are explained by assuming ion pairs, (18), as intermediates.
- Graziano, M. Liliana,Lesce, M. Rosaria,Cinotti, Angela,Scarpati, Rachele
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p. 1833 - 1840
(2007/10/02)
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- Multifunctional Compounds from the 2,5-Peroxide of Methyl Furan-3-carboxylate
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Thermal rearrangement of the title compound (1) leads to the corresponding diepoxide (3) in apolar solvents and to the Δ2-butenolide (2) in basic solvents, whereas the formation of the epoxide (5) is independent of solvent; these conversions represent convenient entries to the syntheses of multifunctional compounds which are structurally related to biologically active products.
- Graziano, M. Liliana,Scarpati, Rachele
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p. 124 - 125
(2007/10/02)
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- Photosensitized Oxidation of Furans; XI. A Simple General Method for the Synthesis of 3-, 4-, or 3,4-Functionalized 5-Hydroxyfuran-2(5H)-ones (4-Hydroxy-2-butenolides)
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The title compounds 3 are prepared, in good yields, by methylene blue photosensitized oxidation of furans 1 in acetone and thermal conversion of the solutions of the intermediate endo-2,5-peroxides 2.
- Graziano, M. L.,Iesce, M. R.
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p. 1151 - 1153
(2007/10/02)
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