Induced diastereoselectivity in photodecarboxylation of 2-phenylpropionic acid in faujasite zeolites

被引:5
作者
Lalitha, A
Pitchumani, K [1 ]
Srinivasan, C
机构
[1] Madurai Kamaraj Univ, Dept Mat Sci, Madurai 625021, Tamil Nadu, India
[2] Madurai Kamaraj Univ, Sch Chem, Madurai 625021, Tamil Nadu, India
关键词
diastereoselectivity; photodecarboxylation; 2-phenylpropionic acid; faujasite zeolites;
D O I
10.1016/S0040-4020(01)00377-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Irradiation of 2-phenylpropionic acid in various cation-exchanged faujasites leads to predominant formation of dl-2,3-diphenylbutane over the meso-isomer tin marked contrast to photolysis in isotropic media) and this zeolite-induced diastereoselectivity is attributed to steric and electronic factors. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4455 / 4459
页数:5
相关论文
共 13 条
[1]   PHOTOCHEMISTRY OF DIASTEREOMERIC 2,4-DIPHENYLPENTAN-3-ONES AND RELATED KETONES IN SUPER-CAGE ENVIRONMENTS PROVIDED BY MICELLES, POROUS-GLASS, AND POROUS SILICA - TEMPERATURE AND MAGNETIC-FIELD EFFECTS [J].
BARETZ, BH ;
TURRO, NJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (05) :1309-1316
[2]   PHOTOLYTIC DEGRADATION OF IBUPROFEN - TOXICITY OF THE ISOLATED PHOTOPRODUCTS ON FIBROBLASTS AND ERYTHROCYTES [J].
CASTELL, JV ;
GOMEZ, MJ ;
MIRANDA, MA ;
MORERA, IM .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1987, 46 (06) :991-996
[3]   MOLECULAR MECHANISM OF NAPROXEN PHOTOSENSITIZATION IN RED BLOOD-CELLS [J].
COSTANZO, LL ;
DEGUIDI, G ;
CONDORELLI, G ;
CAMBRIA, A ;
FAMA, M .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 1989, 3 (02) :223-235
[4]   MOLECULAR MECHANISM OF DRUG PHOTOSENSITIZATION .2. PHOTOHEMOLYSIS SENSITIZED BY KETOPROFEN [J].
COSTANZO, LL ;
DEGUIDI, G ;
CONDORELLI, G ;
CAMBRIA, A ;
FAMA, M .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1989, 50 (03) :359-365
[5]   Direct observation of the benzyl radical and the benzyl anion within cation-exchanged zeolites. A nanosecond laser study [J].
Cozens, FL ;
Ortiz, W ;
Schepp, NP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (51) :13543-13544
[6]   DIASTEREOSELECTIVE INDUCTION IN RADICAL COUPLING REACTIONS - PHOTOLYSIS OF 2,4-DIPHENYLPENTAN-3-ONES ADSORBED ON FAUJASITE ZEOLITES [J].
GHATLIA, ND ;
TURRO, NJ .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1991, 57 (1-3) :7-19
[7]  
JIMENEZ MC, 1995, TETRAHEDRON, V51, P2953
[8]   Photochemistry of 2-(3-benzoylphenyl)propionic acid (ketoprofen) .1. A picosecond and nanosecond time resolved study in aqueous solution [J].
Monti, S ;
Sortino, S ;
DeGuidi, G ;
Marconi, G .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS, 1997, 93 (13) :2269-2275
[9]   MODIFICATION OF PHOTOCHEMICAL REACTIVITY BY ZEOLITES - NORRISH TYPE-I AND TYPE-II REACTIONS OF KETONES AS PHOTOCHEMICAL PROBES OF THE INTERIOR OF ZEOLITES [J].
RAMAMURTHY, V ;
CORBIN, DR ;
EATON, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (18) :5269-5278
[10]   SPECTROSCOPIC STUDIES OF CUTANEOUS PHOTOSENSITIZING AGENTS .4. THE PHOTOLYSIS OF BENOXAPROFEN, AN ANTI-INFLAMMATORY DRUG WITH PHOTO-TOXIC PROPERTIES [J].
RESZKA, K ;
CHIGNELL, CF .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1983, 38 (03) :281-291