Curious reduction products from a strained polycyclic quinone

被引：12

作者：

Zhang, JJ ^{[1
]}

Ho, DM ^{[1
]}

Pascal, RA ^{[1
]}

机构：

[1] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 20期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(99)00643-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sodium borohydride reduction of 9,11,20,22-tetraphenyltetrabenzo[a,c,l,n]pentacene-10,21- dione (1), a strained polycyclic quinone, followed by an aqueous workup does not give the conventional hydroquinone 2. Instead, reduction of an adjacent aromatic ring leads to the cis-9,22-dihydro compound 3 in which steric crowding is substantially relieved. (C) 1999 Elsevier Science Ltd. All rights reserved.

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收藏

页码：3859 / 3862

页数：4

相关论文

共 10 条

[1] SYNTHESIS OF HYDROQUINONE DIACETATES FROM POLYCYCLIC AROMATIC QUINONES [J].

CHO, H ;

HARVEY, RG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (08) :836-839

[2] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[3] SYNTHESIS AND UNUSUAL PROPERTIES OF A HELICALLY TWISTED MULTIPLY METALATED RUBRENE DERIVATIVE [J].

FAGAN, PJ ;

WARD, MD ;

CASPAR, JV ;

CALABRESE, JC ;

KRUSIC, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (09) :2981-2983

[4] Processing of X-ray diffraction data collected in oscillation mode [J].

Otwinowski, Z ;

Minor, W .

MACROMOLECULAR CRYSTALLOGRAPHY, PT A, 1997, 276 :307-326

[5] SYNTHESIS AND STRUCTURE OF LONGITUDINALLY TWISTED POLYCYCLIC AROMATIC-HYDROCARBONS [J].

PASCAL, RA ;

MCMILLAN, WD ;

VANENGEN, D ;

EASON, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) :4660-4665

[6] THE SOLID-STATE STRUCTURE OF 9,11,20,22-TETRAPHENYLTETRABENZO[A,C,L,N]PENTACENE-10,21-DIONE - A LONGITUDINALLY TWISTED MOLECULAR RIBBON [J].

PASCAL, RA ;

VANENGEN, D .

TETRAHEDRON LETTERS, 1987, 28 (03) :293-294

[7] 9,18-DIPHENYLTETRABENZ[A,C,H,J]ANTHRACENE - A REMARKABLY TWISTED POLYCYCLIC AROMATIC HYDROCARBON [J].

PASCAL, RA ;

MCMILLAN, WD ;

VANENGEN, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (18) :5652-5653

[8] Octaphenylnaphthalene and decaphenylanthracene [J].

Qiao, XX ;

Padula, MA ;

Ho, DM ;

Vogelaar, NJ ;

Schutt, CE ;

Pascal, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (04) :741-745

[9] An extraordinarily twisted polycyclic aromatic hydrocarbon [J].

Qiao, XX ;

Ho, DM ;

Pascal, RA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1531-1532

[10]

SHELDRICK GM, 1996, SHELXTL VERSION 5