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].
📜 SIMILAR VOLUMES
The reaction of singlet oxygen with 2-cyclopenten-l-one derivatives is regioselective. Reactivity toward singlet oxygen is not solely determined by the conformation of the carbonyl group relative to the olefinic double bond, since even some s-tran.s derivatives are reasonably reactive.
## Abstract Pyranylium perchlorates with azulen‐1‐yl moiety in 4‐position and thiophen‐2‐yl or furan‐2‐yl in 2 and 6‐positions were obtained by the substitution of 4‐chloro corresponding salts with azulenes. The pyranylium salts are used as starting materials for the synthesis of pyridine and pyrid