A new synthetic method for rotaxanes via tandem Claisen rearrangement, diesterification, and aminolysis

被引：38

作者：

Hiratani, K

Suga, J

Nagawa, Y

Houjou, H

Tokuhisa, H

Numata, M

Watanabe, K

机构：

[1] Utsunomiya Univ, Dept Appl Chem, Utsunomiya, Tochigi 3218585, Japan

[2] Natl Inst Adv Ind Sci & Technol, Nanoarchitecton Res Ctr, Tsukuba, Ibaraki 3058562, Japan

[3] Tokyo Univ Sci, Dept Ind Chem, Chiba 2788510, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 33期

关键词：

rotaxanes; crownophanes; tandem Claisen rearrangement; covalent bond formation; aminolysis;

D O I：

10.1016/S0040-4039(02)01201-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel methodology to make rotaxanes via covalent bond formation has been developed. Rotaxanes composed of crownophanes having two phenolic hydroxy groups as a molecular rotor and an axle having diamide moieties were synthesized in moderate yields via three step processes: tandem Claisen rearrangement, intramolecular diesterification, and aminolysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：5747 / 5750

页数：4

相关论文

共 22 条

[1] Interlocked and intertwined structures and superstructures [J].

Amabilino, DB ;

Stoddart, JF .

CHEMICAL REVIEWS, 1995, 95 (08) :2725-2828

[2] Photoinduction of fast, reversible translational motion in a hydrogen-bonded molecular shuttle [J].

Brouwer, AM ;

Frochot, C ;

Gatti, FG ;

Leigh, DA ;

Mottier, L ;

Paolucci, F ;

Roffia, S ;

Wurpel, GWH .

SCIENCE, 2001, 291 (5511) :2124-2128

[3] Electronically configurable molecular-based logic gates [J].

Collier, CP ;

Wong, EW ;

Belohradsky, M ;

Raymo, FM ;

Stoddart, JF ;

Kuekes, PJ ;

Williams, RS ;

Heath, JR .

SCIENCE, 1999, 285 (5426) :391-394

[4] SYNTHESIS OF MACROCYCLIC POLYETHER COMPOUNDS DERIVED FROM 1,10-PHENANTHROLINE 2,9-DIPHENYL [J].

DIETRICHBUCHECKER, CO ;

SAUVAGE, JP .

TETRAHEDRON LETTERS, 1983, 24 (46) :5091-5094

[5] CHEMICAL TOPOLOGY [J].

FRISCH, HL ;

WASSERMAN, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (18) :3789-&

[6] Transition-metal-directed assembly of well-defined organic architectures possessing large voids: From macrocycles to [2]catenanes [J].

Fujita, M ;

Ogura, K .

COORDINATION CHEMISTRY REVIEWS, 1996, 148 :249-264

[7] THE MOLECULAR NECKLACE - A ROTAXANE CONTAINING MANY THREADED ALPHA-CYCLODEXTRINS [J].

HARADA, A ;

LI, J ;

KAMACHI, M .

NATURE, 1992, 356 (6367) :325-327

[8] SYNTHESIS OF A STABLE COMPLEX OF A MACROCYCLE AND A THREADED CHAIN [J].

HARRISON, IT ;

HARRISON, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (22) :5723-&

[9] Synthesis of novel crownophanes containing two phenolic moieties via a tandem Claisen rearrangement [J].

Hiratani, K ;

Uzawa, H ;

Kasuga, K ;

Kambayashi, H .

TETRAHEDRON LETTERS, 1997, 38 (52) :8993-8996

[10] Tandem claisen rearrangement: A novel, one-step synthesis of calixarene analogues from macrocyclic polyethers [J].

Hiratani, K ;

Kasuga, K ;

Goto, M ;

Uzawa, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (51) :12677-12678