Wavelength-dependent selectivity in [4+4]-cycloaddition reactions

被引:19
作者
Bailey, David [1 ]
Williams, Vance E. [1 ]
机构
[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
关键词
D O I
10.1021/jo060838q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Selective excitation of a variety of anthracene derivatives in the presence of anthracene led to the formation of only the cross-cyclomer products, while irradiating these mixtures at wavelengths where anthracene also absorbs led to both dianthracene and the mixed cyclomers being formed. This method was shown to be general, so long as the chromophore was inert toward forming its homodimer and could be irradiated at wavelengths at which anthracene does not absorb.
引用
收藏
页码:5778 / 5780
页数:3
相关论文
共 18 条
[1]   Complementarity in bimolecular photochromism [J].
Bailey, D ;
Williams, VE .
CHEMICAL COMMUNICATIONS, 2005, (20) :2569-2571
[2]   An efficient synthesis of substituted anthraquinones and naphthoquinones [J].
Bailey, D ;
Williams, VE .
TETRAHEDRON LETTERS, 2004, 45 (12) :2511-2513
[3]   Photodimerization of anthracenes in fluid solution: structural aspects [J].
Bouas-Laurent, H ;
Castellan, A ;
Desvergne, JP ;
Lapouyade, R .
CHEMICAL SOCIETY REVIEWS, 2000, 29 (01) :43-55
[4]   Photodimerization of anthracenes in fluid solutions: (part 2) mechanistic aspects of the photocycloaddition and of the photochemical and thermal cleavage [J].
Bouas-Laurent, H ;
Castellan, A ;
Desvergne, JP ;
Lapouyade, R .
CHEMICAL SOCIETY REVIEWS, 2001, 30 (04) :248-263
[5]   CROSSED PHOTODIMERISATION IN SOLUTION BETWEEN DONOR AND ACCEPTOR ANTHRACENIC MONOMERS [J].
BOUASLAURENT, H ;
LAPOUYAD.R .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (14) :817-+
[6]  
BOUASLAURENT H, 1967, CR ACAD SCI C CHIM, V12, P1061
[7]   PHOTOPOLYMERIZATION .4. PHOTOPOLYMERIZATION OF BISANTHRACENES [J].
DESCHRYVER, FC ;
ANAND, L ;
SMETS, G ;
SWITTEN, J .
JOURNAL OF POLYMER SCIENCE PART B-POLYMER LETTERS, 1971, 9 (10) :777-+
[8]   Photochemical ligation of DNA conjugates through anthracene cyclodimer formation and its fidelity to the template sequences [J].
Ihara, T ;
Fujii, T ;
Mukae, M ;
Kitamura, Y ;
Jyo, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) :8880-8881
[9]   Photochemical cross-linking of poly(ethylene terephthalate-co-2,6-anthracenedicarboxylate) [J].
Jones, JR ;
Liotta, CL ;
Collard, DM ;
Schiraldi, DA .
MACROMOLECULES, 2000, 33 (05) :1640-1645
[10]  
LAPOUYADE R, 1969, CR ACAD SCI C CHIM, V268, P217