Coerced photodimerization reaction in the solid state through amine salt formation

被引:37
作者
Ito, Y [1 ]
Kitada, T [1 ]
Horiguchi, M [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Synth Chem & Biol Chem, Kyoto 6158510, Japan
关键词
solid state; photodimerization; fumaric acid; cinnamic acid; amine salt; imidazole;
D O I
10.1016/S0040-4020(03)01140-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photodimerization of fumaric or several gamma-form trans-cinnamic acids proceeded successfully in the solid state through amine salt formation with ammonia or some aromatic heterocyclic amines (especially, imidazole). It appears that this success is due to a small size or a planar structure of the amine. A layered or a channel-type clathrate crystal structure was revealed, respectively. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7323 / 7329
页数:7
相关论文
共 36 条
[1]   Diastereospecific photochemical dimerization of a stilbene-containing daisy chain monomer in solution as well as in the solid state [J].
Amirsakis, DG ;
Elizarov, AM ;
Garcia-Garibay, MA ;
Glink, PT ;
Stoddart, JF ;
White, AJP ;
Williams, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (10) :1126-1132
[2]  
Amirsakis DG, 2001, ANGEW CHEM INT EDIT, V40, P4256, DOI 10.1002/1521-3773(20011119)40:22<4256::AID-ANIE4256>3.0.CO
[3]  
2-S
[4]  
[Anonymous], 1987, ORG PHOTOCHEM
[5]  
ARSHNEY DB, 2002, J CHEM SOC CHEM COMM, P1964
[6]   Templated photochemical synthesis of a uracil vs. thymine receptor [J].
Bassani, DM ;
Sallenave, X ;
Darcos, V ;
Desvergne, JP .
CHEMICAL COMMUNICATIONS, 2001, (16) :1446-1447
[7]   Supramolecular catalysis of olefin [2+2] photodimerization [J].
Bassani, DM ;
Darcos, V ;
Mahony, S ;
Desvergne, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (36) :8795-8796
[8]   PHOTODIMERS OF CINNAMIC ACID AND RELATED COMPOUNDS - STEREOCHEMICAL STUDY BY ELECTRON-IMPACT AND FIELD DESORPTION MASS-SPECTROMETRY [J].
CACCAMESE, S ;
MONTAUDO, G ;
PRZYBYLSKI, M .
ORGANIC MASS SPECTROMETRY, 1974, 9 (11) :1114-1123
[9]   TOPOCHEMISTRY .2. PHOTOCHEMISTRY OF TRANS-CINNAMIC ACIDS [J].
COHEN, MD ;
SCHMIDT, GMJ ;
SONNTAG, FI .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JUN) :2000-&
[10]   CHEMISTRY OF PHOTODIMERS OF MALEIC AND FUMARIC ACID DERIVATIVES .1. DIMETHYL FUMARATE DIMER [J].
GRIFFIN, GW ;
VELLTURO, AF ;
FURUKAWA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (12) :2725-+