121643-59-2Relevant academic research and scientific papers
Photosensitized oxidation of furans; Part 18: A simple method for a one-pot synthesis of functionalized methyl cis-4-oxoalk-2-enoates
Iesce,Cermola,Piazza,Scarpati,Graziano
, p. 439 - 443 (2007/10/02)
Functionalized methyl cis-4-oxoalk-2-enoates 2 are synthesized in a one-pot procedure by singlet oxygen oxygenation of the corresponding 2-methoxyfurans 1 in methanol and reduction of the resulting hydroperoxides 4 and 5 by the sulfides 6 which are selectively oxidized into the sulfoxides 7. The synthetic method has a wide range of applicability and affords compounds 2 stereoselectively and in good yields; concomitantly the sulfoxides 7 are obtained in excellent yields.
Photosensitized oxidation of furans; part 17: A simple method for the synthesis of 5-hydroperoxyfuran-2(5H)-ones
Iesce,Cermola,Graziano,Scarpati
, p. 944 - 948 (2007/10/02)
The 5-hydroperoxyfuran-2(5H)-ones 3 are synthesized by acid hydrolysis of the dihydrofurans 1 which are prepared in one-pot procedure by reaction of the corresponding furans 4 with singlet oxygen and methanol. The synthetic method has a wide range of applicability; however, compounds 3 unsubstituted at C-4 cannot be prepared since the corresponding dihydrofurans 1 are not formed.
Photosensitized Oxidation of Furans. Part 14. Nature of Intermediates in Thermal Rearrangement of Some endo-Peroxides of 2-Alkoxyfurans: New Rearrangement Pathway of Furan endo-Peroxides
Graziano, M. Liliana,Iesce, M. Rosaria,Cimminiello, Guido,Scarpati, Rachele
, p. 241 - 245 (2007/10/02)
2-Methoxy-5-phenylfurans (1a-c) substituted at C-4 with electron-withdrawing groups, by dye-sensitized photo-oxygenation in non-participating solvents, give the endo-peroxides (3a-c) which by thermal rearrangement partly yield the 3H-1,2-dioxoles (14a-c).The latter, which are the first examples of this ring system, are thermally very unstable.Their formation can be deduced only from the products obtained by thermal rearragement which are structurally related with the thermal rearrangement products of 3H-1,2,4-dioxazoles (10).The behavior of the furans (1a-c) contrasts with that of the 2-methoxy-5-phenylfurans unsubstituted at C-4 which under the same conditions give carbonyl oxides.
