Dynamic hemicarcerands and hemicarceplexes

被引:100
作者
Ro, S [1 ]
Rowan, SJ [1 ]
Pease, AR [1 ]
Cram, DJ [1 ]
Stoddart, JF [1 ]
机构
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
关键词
D O I
10.1021/ol005962p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The reversible nature of the imine bond formation in CDCl3 solution has been exploited to exchange substituted for unsubstituted m-phenylenediamine (MPD) units in hemicarcerand octaimines. Moreover, acid-catalyzed imine exchange has been shown to provide a novel mechanism whereby ferrocene (Fc) can be released as an entrapped guest from the hemicarceplex C(2)B(4)circle dot Fc dissolved in CDCl3 to give the hemicarcerand C2B4 when excess of both MPD and trifluoroacetic acid are present.
引用
收藏
页码:2411 / 2414
页数:4
相关论文
共 40 条
[1]   Rotaxane or pseudorotaxane? That is the question! [J].
Ashton, PR ;
Baxter, I ;
Fyfe, MCT ;
Raymo, FM ;
Spencer, N ;
Stoddart, JF ;
White, AJP ;
Williams, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (10) :2297-2307
[2]   Thermodynamically-controlled cyclisation and interconversion of oligocholates: metal ion templated 'living' macrolactonisation [J].
Brady, PA ;
Sanders, JKM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (21) :3237-3253
[3]   Rotaxane formation under thermodynamic control [J].
Cantrill, SJ ;
Rowan, SJ ;
Stoddart, JF .
ORGANIC LETTERS, 1999, 1 (09) :1363-1366
[4]   Reversible molecular capsules composed of two cavitands linked via an assortment of charged-hydrogen bonds and covalent bonds [J].
Chapman, RG ;
Sherman, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (38) :9818-9826
[5]   Covalent self-assembly of a dimeric borazaaromatic macrocycle [J].
Comina, PJ ;
Philp, D ;
Kariuki, BM ;
Harris, KDM .
CHEMICAL COMMUNICATIONS, 1999, (22) :2279-2280
[6]   Self-assembling capsules [J].
Conn, MM ;
Rebek, J .
CHEMICAL REVIEWS, 1997, 97 (05) :1647-1668
[7]   Dynamic combinatorial libraries of pseudo-peptide hydrazone macrocycles [J].
Cousins, GRL ;
Poulsen, SA ;
Sanders, JKM .
CHEMICAL COMMUNICATIONS, 1999, (16) :1575-1576
[8]   HOST-GUEST COMPLEXATION .63. CONSTRICTIVE AND INTRINSIC BINDING IN A HEMICARCERAND CONTAINING 4 PORTALS [J].
CRAM, DJ ;
BLANDA, MT ;
PAEK, K ;
KNOBLER, CB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) :7765-7773
[9]  
CRAM DJ, 1994, CONTAINER MOL THEIR, P149
[10]   Deracemization by enantiodifferentiating inversion in 1,3-diols [J].
Davis, AP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (06) :591-594