Synthesis of expanded planar dehydrobenzoannulenes: Weakly diatropic, weakly paratropic, or atropic?

被引：32

作者：

Wan, WB ^{[1
]}

Kimball, DB ^{[1
]}

Haley, MM ^{[1
]}

机构：

[1] Univ Oregon, Dept Chem, Eugene, OR 97403 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 38期

关键词：

annulene; aromaticity; alkynes;

D O I：

10.1016/S0040-4039(98)01583-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Use of a Cu/Pd cross-coupling strategy has led to the synthesis of the first dehydrobenzoannulenes containing triacetylenic linkages. NMR studies of these macrocycles and comparison with other known systems indicate that, in spite of their large size and extensive benzannelation, dehydrobenzoannulenes possess weak induced ring currents. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：6795 / 6798

页数：4

相关论文

共 18 条

[1]

BALDWIN KP, 1905, SYNLETT, P1215

[2] Synthesis, crystal structure, and explosive decomposition of 1,2:5,6:11,12:15,16-tetrabenzo-3,7,9,13,17,19-hexadehydro[20]annulene: Formation of onion- and tube-like closed-shell carbon particles [J].

Boese, R ;

Matzger, AJ ;

Vollhardt, KPC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (08) :2052-2053

[3]

Brandsma L, 1988, PREPARATIVE ACETYLEN

[4]

Ciorba V., 1987, ANNULENES BENZO HETE, VI

[5] SYNTHESIS OF MARASIN AND 9-ME-MARASIN, (NONA-6,8-DIYNE-3,4-DIENOL AND DECA-6,8-DIYNE-3,4-DIENOL) [J].

DEGRAAF, W ;

SMITS, A ;

BOERSMA, J ;

VANKOTEN, G ;

HOEKSTRA, WPM .

TETRAHEDRON, 1988, 44 (21) :6699-6704

[6] SILYLATION AS A PROTECTIVE METHOD IN CADIOT-CHODKIEWICZ COUPLINGS - SYNTHESIS OF ARYL-BUTADIYNES AND ARYL-HEXATRIYNES [J].

EASTMOND, R ;

WALTON, DRM .

TETRAHEDRON, 1972, 28 (17) :4591-&

[7]

Garratt P. J., 1986, Aromaticity

[8] One-pot desilylation/dimerization of ethynyl- and butadiynyltrimethylsilanes. Synthesis of tetrayne-linked dehydrobenzoannulenes. [J].

Haley, MM ;

Bell, ML ;

Brand, SC ;

Kimball, DB ;

Pak, JJ ;

Wan, WB .

TETRAHEDRON LETTERS, 1997, 38 (43) :7483-7486

[9] Carbon networks based on dehydrobenzoannulenes: Synthesis of graphdiyne substructures [J].

Haley, MM ;

Brand, SC ;

Pak, JJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (08) :836-838

[10] Versatile synthetic route to and DSC analysis of dehydrobenzoannulenes: Crystal structure of a heretofore inaccessible [20]annulene derivative [J].

Haley, MM ;

Bell, ML ;

English, JJ ;

Johnson, CA ;

Weakley, TJR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (12) :2956-2957