The reaction of variously N-substituted α -furanamides with singlet oxygen has been examined. In addition to the expected fragmentation products the reaction affords rearranged 5-hydroxy- and 5-aryloxy-2(5H)-furanones. Products distribution depends on diverse factors: the presence of α -hydrogen, the presence of the amidic group, the nature and the number of nitrogen substituents. The rearrangement to 5-aryloxy-2(5H)- furanones is unreported.
Rearrangements vs fragmentations in the dye-sensitized photooxygenation of N-aryl α-Furanamides / Iesce, MARIA ROSARIA; Cermola, Flavio; Sferruzza, Rosalia; DELLA GRECA, Marina. - In: CURRENT ORGANIC CHEMISTRY. - ISSN 1385-2728. - 20:20(2016), pp. 2117-2124. [10.2174/1385272820666160505123742]
Rearrangements vs fragmentations in the dye-sensitized photooxygenation of N-aryl α-Furanamides
IESCE, MARIA ROSARIA;CERMOLA, FLAVIO;SFERRUZZA, ROSALIA;DELLA GRECA, MARINA
2016
Abstract
The reaction of variously N-substituted α -furanamides with singlet oxygen has been examined. In addition to the expected fragmentation products the reaction affords rearranged 5-hydroxy- and 5-aryloxy-2(5H)-furanones. Products distribution depends on diverse factors: the presence of α -hydrogen, the presence of the amidic group, the nature and the number of nitrogen substituents. The rearrangement to 5-aryloxy-2(5H)- furanones is unreported.| File | Dimensione | Formato | |
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