A cyclic oligophenylene containing two 1,8-naphthalene units bridged by two face to-face biphenyl linkages exhibiting unusual strain and π-π interaction

被引:49
作者
Iyoda, M [1 ]
Kondo, T [1 ]
Nakao, K [1 ]
Hara, K [1 ]
Kuwatani, Y [1 ]
Yoshida, M [1 ]
Matsuyama, H [1 ]
机构
[1] Tokyo Metropolitan Univ, Grad Sch Sci, Dept Chem, Hachioji, Tokyo 1920397, Japan
关键词
D O I
10.1021/ol0001012
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
GRAPHICS 1,8-[1,8-Naphthalenediylbis(4',4-biphenyldiyl)]naphthalene, a very stable strained cyclophane, has been synthesized in moderate yield using the copper-catalyzed coupling of 1,8-bis(4-(tributylstannyl)phenyl)naphthalene The X-ray analysis of the titled compound discloses bent p,p'-biphenylylene chains with splayed naphthalene rings, and the p,p'-biphenylylene chains located face to face indicate a fairly strong pi-pi interaction.
引用
收藏
页码:2081 / 2083
页数:3
相关论文
共 38 条
[11]   THE RADICAL-ANIONS AND TRIANIONS OF 1,8-DIPHENYLNAPHTHALENE AND OF SOME OF ITS DERIVATIVES CONTAINING A CYCLOPHANE SUBSTRUCTURE [J].
GERSON, F ;
HECKENDORN, R ;
MOCKEL, R .
HELVETICA CHIMICA ACTA, 1985, 68 (07) :1923-1932
[12]   PARAMAGNETIC REDOX STAGES OF A BISPHANE - AN ESR AND ENDOR STUDY [J].
GERSON, F ;
SCHOLZ, M ;
DEMEIJERE, A ;
KONIG, B ;
HEINZE, J ;
MEERHOLZ, K .
HELVETICA CHIMICA ACTA, 1992, 75 (07) :2307-2316
[13]  
Hensel V, 1999, CHEM-EUR J, V5, P421, DOI 10.1002/(SICI)1521-3765(19990201)5:2<421::AID-CHEM421>3.0.CO
[14]  
2-D
[15]   Repetitive construction of macrocyclic oligophenylenes [J].
Hensel, V ;
Lützow, K ;
Jacob, J ;
Gessler, K ;
Saenger, W ;
Schlüter, AD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) :2654-2656
[16]  
HOPE H, 1972, ACTA CRYSTALL B-STRU, VB 28, P1733, DOI 10.1107/S0567740872004947
[17]   SYNTHESIS OF SOME DIPHENYL AND TRIPHENYL DERIVATIVES OF ANTHRACENE AND NAPHTHALENE [J].
HOUSE, HO ;
CAMPBELL, WJ ;
KOEPSELL, DG .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (07) :1003-&
[18]   PREPARATION AND CONFORMATIONAL PROPERTIES OF SEVERAL 1,8-DIARYLNAPHTHALENES [J].
IBUKI, E ;
OZASA, S ;
FUJIOKA, Y ;
MIZUTANI, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (03) :845-851
[19]   CONJUGATION IN MACROCYCLIC SYSTEMS .17. OVERCROWDED COMPOUND .8. CRYSTAL AND MOLECULAR STRUCTURES OF HEX META PHENYLENE AND PENTA META PHENYLENE [J].
IRNGARTI.H ;
LEISEROW.L ;
SCHMIDT, MJ .
CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (04) :1132-&
[20]   CRYSTAL STRUCTURE OF AN OVERCROWDED AROMATIC COMPOUND - 3-BROMO-1,8-DIMETHYLNAPHTHALENE [J].
JAMESON, MB ;
PENFOLD, BR .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JAN) :528-&