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Photooxygenation of alditol-1-C-yl derivatives of furan with singlet oxygen

✍ Scribed by JoséManuel Bánez Sanz; Diego Galisteo González; Juan Antonio López Sastre; Justo Félix Rodríguez Amo; Cristina Romero-Avila García; Mercedes Santos García; María Ascensión Sanz Tejedor


Book ID
102996505
Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
532 KB
Volume
289
Category
Article
ISSN
0008-6215

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✦ Synopsis


The last two decades have witnessed much interest in the development and analysis of organic substrates which behave as chemical systems capable of selective and catalytic oxygenation with molecular oxygen [1]. Singlet oxygen (~O 2) has been used frequently to carry out such oxidations [2]. Furan and its derivatives, whose synthesis is basically achieved either through reaction of o~-hydroxyaldehydes with 1,3-dicarbonyl compounds or through acid-catalyzed dehydration of carbohydrates [3] as substrates, can be used as acceptors of singlet oxygen to study either reaction kinetics or biological roles [4].

As 1,3-dienes, furans can undergo I o 2 cycloadditions, i.e. selective cis-l,4-dioxygenations, which produces bicyclic endoperoxides whose decomposition yields useful products. Depending on the substituents, the reaction conditions, and the solvents used, furan endoperoxides may be precursors of substituted hydroperoxides or dioxiranes [5]. Furan endoperoxides are of interest in the elucidation of oxidation mechanism such as epoxidation, anomalous ozonolysis, and oxidative decarbonylation [6].


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