Site specificity in the photooxidation of some trisubstituted alkenes in thionin-supported zeolite Na-Y. On the role of the alkali metal cation

被引:46
作者
Stratakis, M [1 ]
Froudakis, G [1 ]
机构
[1] Univ Crete, Dept Chem, Iraklion 71409, Greece
关键词
D O I
10.1021/ol000021y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The less substituted side of some geminal dimethyl trisubstituted alkenes becomes significantly more reactive if photooxygenation takes place in thionin-supported zeolite Na-Y. These results are mainly attributed to a synergistic interaction between the alkali metal cation, the alkene, and the oxygen in the transition state of perepoxide formation.
引用
收藏
页码:1369 / 1372
页数:4
相关论文
共 19 条
[1]  
Barich DH, 1998, ANGEW CHEM INT EDIT, V37, P2530, DOI 10.1002/(SICI)1521-3773(19981002)37:18<2530::AID-ANIE2530>3.0.CO
[2]  
2-2
[3]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[4]   Photooxidations in zeolites. Part 2: A new mechanistic model for reaction selectivity in singlet oxygen ene reactions in zeolitic media [J].
Clennan, EL ;
Sram, JP .
TETRAHEDRON LETTERS, 1999, 40 (29) :5275-5278
[5]  
CLENNAN EL, IN PRESS TETRAHEDRON
[6]  
Frisch M.J., 1995, GAUSSIAN 94 REVISION
[7]   A quantitative basis for a scale of Na+ affinities of organic and small biological molecules in the gas phase [J].
Hoyau, S ;
Norrman, K ;
McMahon, TB ;
Ohanessian, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (38) :8864-8875
[8]   DEVELOPMENT OF THE COLLE-SALVETTI CORRELATION-ENERGY FORMULA INTO A FUNCTIONAL OF THE ELECTRON-DENSITY [J].
LEE, CT ;
YANG, WT ;
PARR, RG .
PHYSICAL REVIEW B, 1988, 37 (02) :785-789
[9]   Selective oxidation of olefins within organic dye cation-exchanged zeolites [J].
Li, XY ;
Ramamurthy, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (43) :10666-10667
[10]   Electron transfer reactions within zeolites: Photooxidation of stilbenes [J].
Li, XY ;
Ramamurthy, V .
TETRAHEDRON LETTERS, 1996, 37 (30) :5235-5238