Construction of a Hemifullerene Skeleton: A Regioselective Intramolecular Oxidative Cyclization

被引：32

作者：

Amaya, Toru ^{[1
]}

Ito, Takanori ^{[1
]}

Hirao, Toshikazu ^{[1
,2
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

[2] JST, ACT C, Kawaguchi, Saitama 3320012, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 18期

基金：

日本学术振兴会;

关键词：

arenes; fullerenes; fused-ring system; regioselectivity; TO-BOWL INVERSION; GEODESIC POLYARENES; STRUCTURAL-ANALYSIS; SUMANENE; CORANNULENE; REARRANGEMENTS; HYDROCARBON; FULLERENES; BUCKYBOWL; COMPLEX;

D O I：

10.1002/anie.201500548

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A two-step synthesis of a strained pi bowl, with hemifullerene skeleton from sumanene, was achieved in a high yield. The first step is a base-promoted condensation reaction with a benzophenone compound, bis(3,5-dimethylphenyl) methanone. The second step is the regioselective intramolecular oxidative cyclization, which is a key reaction for the hemifullerene skeleton synthesis. This regioselective cyclization is likely to be under thermodynamic control. This strategy will allow facile synthesis of various highly strained pi bowls.

引用

页码：5483 / 5487

页数：5

共 58 条

[1] BUCKYBOWLS. 2. TOWARD THE TOTAL SYNTHESIS OF BUCKMINSTERFULLERENE (C-60) - BENZ[5,6]-AS-INDACENO-[3,2,1,8,7-MNOPQR]INDENO[4,3,2,1-CDEF]CHRYSENE [J].

ABDOURAZAK, AH ;

MARCINOW, Z ;

SYGULA, A ;

SYGULA, R ;

RABIDEAU, PW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (23) :6410-6411

[2]

Amaya T., 2010, ANGEW CHEM, V122, P413

[3]

Amaya T., 2007, ANGEW CHEM, V119, P8528

[4] Bowl-to-bowl inversion of sumanene derivatives [J].

Amaya, Toru ;

Sakane, Hiroyuki ;

Muneishi, Toshiko ;

Hirao, Toshikazu .

CHEMICAL COMMUNICATIONS, 2008, (06) :765-767

[5] A concave-bound CpFe complex of sumanene as a metal in a π bowl [J].

Amaya, Toru ;

Sakane, Hiroyuki ;

Hirao, Toshikazu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (44) :8376-8379

[6] Synthesis and characterization of π-extended bowl-shaped π-conjugated molecules [J].

Amaya, Toru ;

Mori, Koichi ;

Wu, Hsyueh-Liang ;

Ishida, Satoshi ;

Nakamura, Jun-ichi ;

Murata, Kazuhiko ;

Hirao, Toshikazu .

CHEMICAL COMMUNICATIONS, 2007, (19) :1902-1904

[7] Chemistry of Sumanene [J].

Amaya, Toru ;

Hirao, Toshikazu .

CHEMICAL RECORD, 2015, 15 (01) :310-321

[8] Sumanenyl Metallocenes: Synthesis and Structure of Mono- and Trinuclear Zirconocene Complexes [J].

Amaya, Toru ;

Takahashi, Yuki ;

Moriuchi, Toshiyuki ;

Hirao, Toshikazu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (36) :12794-12798

[9] Sumanenemonoone Imines Bridged by Redox-Active π-Conjugated Unit: Synthesis, Stepwise Coordination to Palladium(II), and Laser-Induced Formation of Nitrogen-Doped Graphitic Carbon [J].

Amaya, Toru ;

Inada, Yuhi ;

Shimizu, Yasutomo ;

Saeki, Akinori ;

Tsuji, Ryotaro ;

Seki, Shu ;

Hirao, Toshikazu .

CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (09) :2568-2575

[10] Synthesis and Characterization of Bisumanenylidene [J].

Amaya, Toru ;

Ito, Takanori ;

Hirao, Toshikazu .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) :3531-3535

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