Photooxygenation of furans in water and ionic liquid solutions

被引:21
作者
Astarita, Anna [1 ]
Cermola, Flavio [1 ]
DellaGreca, Marina [1 ]
Iesce, Maria Rosaria [1 ]
Previtera, Lucio [1 ]
Rubino, Maria [1 ]
机构
[1] Complesso Univ Monte St Angelo, Dipartimento Chim Organ & Biochim, I-80126 Naples, Italy
关键词
DYE-SENSITIZED PHOTOOXYGENATION; SIMPLE GENERAL-METHOD; PHOTOSENSITIZED OXIDATION; SINGLET OXYGEN; CONVERSION;
D O I
10.1039/b914726h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Photooxygenation of differently functionalized furans is investigated in aqueous solutions and in ionic liquids [emim]Br and [bmim]BF4. The reaction is generally selective and the final products derive from rearrangement of the intermediate endoperoxides, depending mainly on the polarity and/or nucleophilic nature of the solvent.
引用
收藏
页码:2030 / 2033
页数:4
相关论文
共 29 条
[1]   SYNTHESIS OF METHYL 2,3-DIDEOXY-DL-ALK-2-ENOPYRANOSIDES FROM FURAN COMPOUNDS - GENERAL APPROACH TO TOTAL SYNTHESIS OF MONOSACCHARIDES [J].
ACHMATOWICZ, O ;
BUKOWSKI, P ;
SZECHNER, B ;
ZWIERZCHOWSKA, Z ;
ZAMOJSKI, A .
TETRAHEDRON, 1971, 27 (10) :1973-+
[2]  
[Anonymous], 2008, Handbook of green chemistry and technology
[3]   Dye-sensitized photooxygenation of sugar furans: novel bis-epoxide and spirocyclic C-nucleosides [J].
Astarita, Anna ;
Cermola, Flavio ;
Iesce, M. Rosaria ;
Previtera, Ludo .
TETRAHEDRON, 2008, 64 (28) :6744-6748
[4]   Reaction of Singlet Oxygen with Thioanisole in Ionic Liquids: a Solvent Induced Mechanistic Dichotomy [J].
Baciocchi, Enrico ;
Chiappe, Cinzia ;
Del Giacco, Tiziana ;
Fasciani, Chiara ;
Lanzalunga, Osvaldo ;
Lapi, Andrea ;
Melai, Bernardo .
ORGANIC LETTERS, 2009, 11 (06) :1413-1416
[5]   Dye-sensitized photooxygenation of furanosyl furans:: Synthesis of a new pyridazine C-nucleoside [J].
Cermola, F ;
Iesce, MR ;
Buonerba, G .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6503-6505
[6]  
Clennan EL, 2005, MOL SUPRAM PHOTOCHEM, V12, P365
[7]  
COTTIER L, 1986, B SOC CHIM FR, P844
[8]  
DUNLOP AP, 1953, FURANS, P579
[9]   THE PHOTOCHEMICAL-SYNTHESIS OF FINE CHEMICALS WITH SUNLIGHT [J].
ESSER, P ;
POHLMANN, B ;
SCHARF, HD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (20) :2009-2023
[10]   Possible singlet oxygen generation from the photolysis of indigo dyes in methanol, DMSO, water, and ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate [J].
Gandra, Naveen ;
Frank, Aaron T. ;
Le Gendre, Onica ;
Sawwan, Nahed ;
Aebisher, David ;
Liebman, Joel F. ;
Houk, K. N. ;
Greer, Alexander ;
Gao, Ruomei .
TETRAHEDRON, 2006, 62 (46) :10771-10776