CRYSTAL TO MOLECULAR CHIRALITY TRANSFER - SUPRAMOLECULAR PHOTOCHEMISTRY OF CRYSTALLINE CARBOXYLATE SALTS

被引:28
作者
JONES, R [1 ]
SCHEFFER, JR [1 ]
TROTTER, J [1 ]
YANG, J [1 ]
机构
[1] UNIV BRITISH COLUMBIA,DEPT CHEM,VANCOUVER V6T 1Z1,BC,CANADA
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/S0040-4039(00)61122-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Solid state irradiation of a salt formed between a prochiral, photochemically reactive carboxylic acid and a non-absorbing, optically active amine is shown to lead to an optically active Norrish type II photoproduct whose optical purity depends on the dimorphic crystalline modification photolyzed.
引用
收藏
页码:5481 / 5484
页数:4
相关论文
共 15 条
[1]   ABSOLUTE ASYMMETRIC INDUCTION DIFFERENCES IN DUAL PATHWAY PHOTOREACTIONS [J].
CHEN, JX ;
POKKULURI, PR ;
SCHEFFER, JR ;
TROTTER, J .
TETRAHEDRON LETTERS, 1990, 31 (47) :6803-6806
[2]   STEREOSELECTIVITY REVERSAL OF A PHOTOCHEMICAL-REACTION IN THE SOLID-STATE [J].
EVANS, S ;
OMKARAM, N ;
SCHEFFER, JR ;
TROTTER, J .
TETRAHEDRON LETTERS, 1985, 26 (48) :5903-5906
[3]   USE OF CHIRAL SINGLE-CRYSTALS TO CONVERT ACHIRAL REACTANTS TO CHIRAL PRODUCTS IN HIGH OPTICAL YIELD - APPLICATION TO THE DI-PI-METHANE AND NORRISH TYPE-II PHOTOREARRANGEMENTS [J].
EVANS, SV ;
GARCIAGARIBAY, M ;
OMKARAM, N ;
SCHEFFER, JR ;
TROTTER, J ;
WIREKO, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (18) :5648-5650
[4]   REACTIVITY DIFFERENCES BETWEEN DIMORPHS IN A CRYSTALLINE PHASE NORRISH TYPE-II REACTION [J].
EVANS, SV ;
OMKARAM, N ;
SCHEFFER, JR ;
TROTTER, J .
TETRAHEDRON LETTERS, 1986, 27 (13) :1419-1422
[5]   MECHANISTIC PHOTOCHEMISTRY OF 1-ADAMANTYLACETONE [J].
GAGOSIAN, RB ;
DALTON, JC ;
TURRO, NJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (18) :5189-5192
[6]   ASYMMETRIC INDUCTION IN THE SOLID-STATE PHOTOCHEMISTRY OF SALTS OF CARBOXYLIC-ACIDS WITH OPTICALLY-ACTIVE AMINES [J].
GUDMUNDSDOTTIR, AD ;
SCHEFFER, JR .
TETRAHEDRON LETTERS, 1990, 31 (47) :6807-6810
[7]   ASYMMETRIC INDUCTION IN THE SOLID-STATE PHOTOCHEMISTRY OF AMMONIUM-SALTS [J].
GUDMUNDSDOTTIR, AD ;
SCHEFFER, JR .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1991, 54 (04) :535-538
[8]   ENTROPIC CONTROL OF PHOTOCHEMICAL REACTIVITY - TRANSITION-STATE FOR GAMMA-HYDROGEN ABSTRACTION OF ALKYL PHENYL KETONES [J].
LEWIS, FD ;
JOHNSON, RW ;
KORY, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (19) :6100-6107
[9]  
RAMAMURTHY V, 1991, PHOTOCHEMISTRY ORG C, pCH7
[10]   SOME ASPECTS OF PHOTOCHEMICAL AND MASS SPECTRAL BEHAVIOR OF BRIDGEHEAD ACETONE DERIVATIVES [J].
SAUERS, RR ;
GORODETS.M ;
WHITTLE, JA ;
HU, CK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (21) :5520-&