Chemoselective hydroperoxidation of alkenylarenes within thionin-supported zeolite Na-Y

被引：17

作者：

Stratakis, M ^{[1
]}

Rabalakos, C ^{[1
]}

机构：

[1] Univ Crete, Dept Chem, Iraklion 71409, Greece

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 27期

关键词：

zeolite Na-Y; ene reactions; singlet oxygen; zwitterions;

D O I：

10.1016/S0040-4039(01)00739-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photooxidation of several 1-aryl-2-methylpropenes within the thionin-supported zeolite Na-Y affords the ene type allylic hydroperoxides in a highly chemoselective manner. This is in contrast to their photooxygenation reaction in solution, where the e,le pathway is less favorable compared to the [4+2] or [2+2] pathways. Cation-pi interactions are likely to be responsible for this selectivity. (C) 2001 Published by Elsevier Science Ltd.

引用

收藏

页码：4545 / 4547

页数：3

相关论文

共 25 条

[1] pi-Facial diastereoselectivity in the [4+2] cycloaddition of singlet oxygen as a mechanistic probe [J].

Adam, W ;

Prein, M .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (06) :275-283

[2] New mechanistic and synthetic aspects of singlet oxygen chemistry [J].

Clennan, EL .

TETRAHEDRON, 2000, 56 (47) :9151-9179

[3] SYNTHETIC AND MECHANISTIC ASPECTS OF 1,3-DIENE PHOTOOXIDATION [J].

CLENNAN, EL .

TETRAHEDRON, 1991, 47 (08) :1343-1382

[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] Photochemical reactions in the interior of a zeolite. Part 5: The origin of the zeolite induced regioselectivity in the singlet oxygen ene reaction [J].

Clennan, EL ;

Sram, JP .

TETRAHEDRON, 2000, 56 (36) :6945-6950

[6] A complete basis set estimate of cation-π bond strengths:: Na+(ethylene) and Na+(benzene) [J].

Feller, D .

CHEMICAL PHYSICS LETTERS, 2000, 322 (06) :543-548

[7]

FRIMMER AA, 1985, SINGLET OXYGEN REACT, P120

[8] CHEMISTRY OF SINGLET OXYGEN .52. REACTION WITH TRANS-STILBENE [J].

KWON, BM ;

FOOTE, CS ;

KHAN, SI .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) :3378-3382

[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