Effects of strained bicyclic annelation on the benzene nucleus: The X-ray crystal structures of a triphenylene and two anthracene derivatives

被引:26
作者
Cardullo, F
Giuffrida, D
Kohnke, FH
Raymo, FM
Stoddart, JF
Williams, DJ
机构
[1] UNIV MESSINA,DIPARTIMENTO CHIM ORGAN & BIOL,I-98166 MESSINA,ITALY
[2] UNIV BIRMINGHAM,SCH CHEM,BIRMINGHAM B15 2TT,W MIDLANDS,ENGLAND
[3] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,CHEM CRYSTALLOG LAB,LONDON SW7 2AY,ENGLAND
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1996年 / 35卷 / 03期
关键词
bond-length alternation; Mills-Nixon effect; polycycles; strained rings; triepoxytriphenylenes;
D O I
10.1002/anie.199603391
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pronounced bond length alternation in the central aromatic ring is the eye-catching structural feature of triepoxytriphenylene 1. By contrast, no significant bond length alternation is observed in the linearly bisannelated compounds 2 and 3. The key difference is ascribed to the position of annelations with the bicyclic units (Image Presented). © 1996, Wiley-VCH Verlag. All rights reserved.
引用
收藏
页码:339 / 341
页数:3
相关论文
共 34 条
[1]  
AEKEROY CB, 1993, CHEM SOC REV, V22, P397
[2]  
[Anonymous], ANGEW CHEM
[3]   MOLECULAR BELTS .2. SUBSTRATE-DIRECTED SYNTHESES OF BELT-TYPE AND CAGE-TYPE STRUCTURES [J].
ASHTON, PR ;
GIRRESER, U ;
GIUFFRIDA, D ;
KOHNKE, FH ;
MATHIAS, JP ;
RAYMO, FM ;
SLAWIN, AMZ ;
STODDART, JF ;
WILLIAMS, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) :5422-5429
[4]   MOLECULAR LEGO .1. SUBSTRATE-DIRECTED SYNTHESIS VIA STEREOREGULAR DIELS-ALDER OLIGOMERIZATIONS [J].
ASHTON, PR ;
BROWN, GR ;
ISAACS, NS ;
GIUFFRIDA, D ;
KOHNKE, FH ;
MATHIAS, JP ;
SLAWIN, AMZ ;
SMITH, DR ;
STODDART, JF ;
WILLIAMS, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) :6330-6353
[5]  
BALBRIDGE KK, 1992, J AM CHEM SOC, V114, P9583
[6]   THE EFFECT OF FUSION OF ANGULAR STRAINED RINGS ON BENZENE - CRYSTAL-STRUCTURES OF 1,2-DIHYDROCYCLOBUTA[A]CYCLOPROPA[C]-, 1,2,3,4-TETRAHYDRODICYCLOBUTA[A,C]-, 1,2,3,4-TETRAHYDRODICYCLOBUTA[A,C]CYCLOPROPA[E]-, AND 1,2,3,4,5,6-HEXAHYDROTRICYCLOBUTA[A,C,E]BENZENE [J].
BOESE, R ;
BLASER, D ;
BILLUPS, WE ;
HALEY, MM ;
MAULITZ, AH ;
MOHLER, DL ;
VOLLHARDT, KPC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (03) :313-317
[7]  
Boese R., 1994, ANGEW CHEM, V106, P321
[8]   X-RAY-DIFFRACTION EVIDENCE FOR A CYCLOHEXATRIENE MOTIF IN THE MOLECULAR-STRUCTURE OF TRIS(BICYCLO[2.1.1]HEXENO)BENZENE - BOND ALTERNATION AFTER THE REFUTATION OF THE MILLS-NIXON THEORY [J].
BURGI, HB ;
BALDRIDGE, KK ;
HARDCASTLE, K ;
FRANK, NL ;
GANTZEL, P ;
SIEGEL, JS ;
ZILLER, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (13-14) :1454-1456
[9]   THE RELATIONSHIP BETWEEN PARTIAL BOND FIXATION INDUCED BY THROUGH-BOND AND OR THROUGH-SPACE PERTURBATIONS IN NONPLANAR BENZENE-DERIVATIVES AND H-1 SPIN SPIN COUPLING-CONSTANTS [J].
CRAW, JS ;
HUSH, NS ;
STERNHELL, S ;
TANSEY, CW .
JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (14) :5753-5759
[10]   THE C-H...O HYDROGEN-BOND IN CRYSTALS - WHAT IS IT [J].
DESIRAJU, GR .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (10) :290-296