Synthesis of [2]rotaxanes by tritylative endcapping of in situ formed pseudorotaxanes having thiol or hydroxyl functionality on the axle termini

被引：23

作者：

Furusho, Y ^{[1
]}

Rajkumar, GA ^{[1
]}

Oku, T ^{[1
]}

Takata, T ^{[1
]}

机构：

[1] Univ Osaka Prefecture, Grad Sch Engn, Dept Appl Chem, Sakai, Osaka 5998531, Japan

来源：

TETRAHEDRON | 2002年 / 58卷 / 33期

基金：

日本学术振兴会;

关键词：

2]rotaxane; tritylation; pseudorotaxane; thiol; alcohol; endcapping;

D O I：

10.1016/S0040-4020(02)00749-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tritylative endcapping of an in situ formed pseudorotaxane consisting of dibenzo-24-crown-8 and an axle having a thiol group at the end by treatment with trityl hexafluorophosphate at room temperature gave the corresponding sulfide-type [2]rotaxane in high yields. Treatment of the pseudorotaxane having a hydroxyl group at the axle terminal with trityl hexafluorophophate followed by addition of a base such as triethylamine afforded the corresponding ether-type [2]rotaxane in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：6609 / 6613

页数：5

共 60 条

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

Amabilino, DB ;

Stoddart, JF .

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

[2] DIALKYLAMMONIUM ION CROWN-ETHER COMPLEXES - THE FORERUNNERS OF A NEW FAMILY OF INTERLOCKED MOLECULES [J].

ASHTON, PR ;

CAMPBELL, PJ ;

CHRYSTAL, EJT ;

GLINK, PT ;

MENZER, S ;

PHILP, D ;

SPENCER, N ;

STODDART, JF ;

TASKER, PA ;

WILLIAMS, DJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17) :1865-1869

[3] 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

[4] Pseudorotaxanes formed between secondary dialkylammonium salts and crown ethers [J].

Ashton, PR ;

Chrystal, EJT ;

Glink, PT ;

Menzer, S ;

Schiavo, C ;

Spencer, N ;

Stoddart, JF ;

Tasker, PA ;

White, AJP ;

Williams, DJ .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (06) :709-728

[5]

Ashton PR, 1996, CHEM-EUR J, V2, P729

[6]

Ashton PR, 2000, CHEM-EUR J, V6, P3558, DOI 10.1002/1521-3765(20001002)6:19<3558::AID-CHEM3558>3.0.CO

[7]

2-M

[8] 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

[9] Unique "cradled barbell" complex between a secondary diammonium ion and bis(m-phenylene)-32-crown-10 [J].

Bryant, WS ;

Guzei, IA ;

Rheingold, AL ;

Gibson, HW .

ORGANIC LETTERS, 1999, 1 (01) :47-50

[10] A molecular meccano kit [J].

Cantrill, SJ ;

Pease, AR ;

Stoddart, JF .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (21) :3715-3734

← 1 2 3 4 5 6 →