Macrocyclic cyclophane belts via double diels-alder cycloadditions: Macroannulation of bisdienes by bisdienophiles. Synthesis of a key precursor to an [8]cyclacene

被引：83

作者：

Cory, RM

McPhail, CL

Dikmans, AJ

Vittal, JJ

机构：

[1] Department of Chemistry, University of Western Ontario, London

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 12期

关键词：

D O I：

10.1016/0040-4039(96)00263-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of macrocyclic cyclophanes is accomplished by double Diels-Alder cycloaddition of two bisdienophiles, 1,4,5,8-anthradiquinone and p-phenylenedimaleimide, to a bisdiene, 2,3,6,7-tetraheptylidene-1,2,3,4,5,6,7,8-octahydroanthracene. The structure of the macrocyclic cyclophane derived from the diquinone has been determined by single crystal x-ray diffraction, in addition to H-1 and C-13 NMR HRMS and IR spectroscopic data.

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页码：1983 / 1986

页数：4

相关论文

共 8 条

[1] INTERMEDIATES FOR THE SYNTHESIS OF LINEAR-CHAINS OF 1,2/4,5-FUSED CYCLOHEXA-1,4-DIENE RINGS AND BELTENES BY REPEATED DIELS-ALDER REACTIONS [J].

ALDER, RW ;

ALLEN, PR ;

EDWARDS, LS ;

FRAY, GI ;

FULLER, KE ;

GORE, PM ;

HEXT, NM ;

PERRY, MH ;

THOMAS, AR ;

TURNER, KS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (21) :3071-3077

[2] CYCLOADDITION REACTIONS OF A BISISOBENZOFURAN LEADING TO LINEAR POLYACENEQUINONES AND A QUADRUPLY BRIDGED CYCLOPHANE [J].

CHIBA, T ;

KENNY, PW ;

MILLER, LL .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4327-4331

[3] LINEARLY FUSED RIBBONS OF CARBOCYCLIC 6-MEMBERED RINGS VIA DIELS-ALDER CYCLOADDITIONS .1. MODEL STUDIES AND KEY INTERMEDIATES [J].

CORY, RM ;

MCPHAIL, CL ;

DIKMANS, AJ .

TETRAHEDRON LETTERS, 1993, 34 (47) :7533-7536

[4] THE STRUCTURE-DIRECTED SYNTHESIS OF CYCLACENE AND POLYACENE DERIVATIVES [J].

GIRRESER, U ;

GIUFFRIDA, D ;

KOHNKE, FH ;

MATHIAS, JP ;

PHILP, D ;

STODDART, JF .

PURE AND APPLIED CHEMISTRY, 1993, 65 (01) :119-125

[5] DOUBLE-STRANDED MOLECULES - A [6]BELTENE DERIVATIVE AND THE CORRESPONDING OPEN-CHAIN POLYMER [J].

GODT, A ;

ENKELMANN, V ;

SCHLUTER, AD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (12) :1680-1682

[6] MOLECULAR LADDERS CONSTITUTED OF LATERALLY-FUSED 1,4-CYCLOHEXADIENE SUBUNITS - OPEN-CHAIN MODELS OF THE [N]BELTENES [J].

GRAHAM, RJ ;

PAQUETTE, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5770-5777

[7]

KOHNKE FH, 1993, TOP CURR CHEM, V165, P1

[8]

SCHRODER A, 1994, TOP CURR CHEM, V172, P179