Photocycloaddition of chalcones to yield cyclobutyl ditopic cyclophanes

被引:19
作者
Cibin, FR
Di Bello, N
Doddi, G
Fares, V
Mencarelli, P
Ullucci, E
机构
[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
[2] Univ Roma La Sapienza, CNR, IMC, Sez Meccanismi Reaz, I-00185 Rome, Italy
[3] CNR, Area Ric Roma 1, Sez Monterondo, Ist Cristallog, I-00016 Monterotondo, Italy
关键词
cyclophanes; enones; chalcones; carbocycles; cycloaddition; photochemistry; photocyclization;
D O I
10.1016/j.tet.2003.10.026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The intramolecular photocycloaddition of chalcones to give cyclobutanes has proved to be a fast and convenient method to shrink a cyclophane ring to a tricyclic system, in order to prepare potential ditopic receptors. X-Ray results confirm the previously indicated structure for the cyclobutanes 2a (n=1, m=1), in which the cyclization occurs by a head-to-head syn ring closure. NMR results indicate that the same process occurs for the cyclobutanes 2b (n=2, m=2) and 2c (n=1, m=3). (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9971 / 9978
页数:8
相关论文
共 26 条
[1]   THE PREPARATION OF PHOTORESPONSIVE CYCLOBUTANOCROWN ETHERS BY MEANS OF INTRAMOLECULAR [2+2]PHOTOCYCLOADDITION [J].
AKABORI, S ;
KUMAGAI, T ;
HABATA, Y ;
SATO, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (07) :2459-2466
[2]   THE NOVEL SYNTHESES OF PHOTOREVERSIBLE CYCLOBUTANOCROWN ETHERS BY THE INTRAMOLECULAR PHOTOADDITION OF ALPHA,OMEGA-DICINNAMOYL POLYETHYLENE-GLYCOL DERIVATIVES [J].
AKABORI, S ;
HABATA, Y ;
NAKAZAWA, M ;
YAMADA, Y ;
SHINDO, Y ;
SUGIMURA, T ;
SATO, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (09) :3453-3455
[3]   SYNTHESES OF PHOTORESPONSIVE CYCLOBUTANE-1,2-DICARBONYL-CAPPED 2.N DIAZACROWN ETHERS BY INTRAMOLECULAR [2 + 2]PHOTOCYCLOADDITION AND THE STRUCTURES OF THEIR LITHIUM AND MERCURY(II) COMPLEXES [J].
AKABORI, S ;
KUMAGAI, T ;
HABATA, Y ;
SATO, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08) :1497-1505
[4]  
Burla M. C., 2003, Journal of Applied Crystallography, V36, DOI 10.1107/S0021889803012585
[5]   REVISION OF STEREOCHEMICAL ASSIGNMENT OF A CYCLOBUTANE DERIVATIVE FROM CHALCONE PHOTO-DIMERIZATION VIA X-RAY-DIFFRACTION ANALYSIS [J].
CACCAMESE, S ;
MCMILLAN, JA ;
MONTAUDO, G .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (13) :2703-2704
[6]   Synthesis of a ditopic cyclophane based on the cyclobutane ring by chalcone photocycloaddition [J].
Cibin, FR ;
Doddi, G ;
Mencarelli, P .
TETRAHEDRON, 2003, 59 (19) :3455-3459
[7]   The photochemical dimerization of 3-heteroaryl-acrylates [J].
D'Auria, M ;
Emanuele, L ;
Esposito, V ;
Racioppi, R .
ARKIVOC, 2002, :65-78
[8]   Photochemical dimerization in solution of heterocyclic substituted alkenes bearing an electron withdrawing group [J].
D'Auria, M .
HETEROCYCLES, 2001, 54 (01) :475-496
[9]  
EGERTON PL, 1981, J AM CHEM SOC, V103, P3859, DOI 10.1021/ja00403a039
[10]  
GAWRONSKI J, 1989, CHEM ENONES, P81