Unexpected phenyl group rearrangement during an intramolecular Scholl reaction leading to an alkoxy-substituted hexa-peri-hexabenzocoronene

被引：99

作者：

Dou, Xi

Yang, Xiaoyin

Bodwell, Graham J.

Wagner, Manfred

Enkelmann, Volker

Muellen, Klaus

机构：

[1] Max Planck Inst Polymer Res, D-55128 Mainz, Germany

[2] Mem Univ Newfoundland, Dept Chem, St John, NF A1B 3X7, Canada

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 13期

关键词：

D O I：

10.1021/ol0708018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple dimethoxy-substituted hexa-peri-hexabenzocoronene (m-dimethoxy HBC) was unexpectedly obtained along with a bis-spirocyclic dienone during an intramolecular Scholl reaction of its para isomer.

引用

页码：2485 / 2488

页数：4

共 25 条

[1]

[Anonymous], FRIEDEL CRAFTS RELAT

[2]

Curtin D.Y., 1954, RECENT CHEM PROG, V15, P111

[3] Rearrangements involving the phenonium ion:: A theoretical investigation [J].

del Río, E ;

Menéndez, MI ;

López, R ;

Sordo, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (21) :5064-5068

[4] Oxidative cyclodehydrogenation reaction for the design of extended 2D and 3D carbon nanostructures:: A theoretical study [J].

Di Stefano, M ;

Negri, F ;

Carbone, P ;

Müllen, K .

CHEMICAL PHYSICS, 2005, 314 (1-3) :85-99

[5] Structurally characterized hetero-oligopolyphenylenes: Synthetic advances toward next-generation heterosuperbenzenes [J].

Gregg, DJ ;

Ollagnier, CMA ;

Fitchett, CM ;

Draper, SM .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (11) :3043-3052

[6] The chemistry of organic nanomaterials [J].

Grimsdale, AC ;

Müllen, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (35) :5592-5629

[7]

Iyer VS, 1998, ANGEW CHEM INT EDIT, V37, P2696, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2696::AID-ANIE2696>3.0.CO

[8]

2-E

[9] A CYCLOADDITION CYCLODEHYDROGENATION ROUTE FROM STILBENOIDS TO EXTENDED AROMATIC-HYDROCARBONS [J].

MULLER, M ;

MAUERMANNDULL, H ;

WAGNER, M ;

ENKELMANN, V ;

MULLEN, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (15) :1583-1586

[10] Polycyclic aromatic hydrocarbons by cyclodehydrogenation and skeletal rearrangement of oligophenylenes [J].

Muller, M ;

Iyer, VS ;

Kubel, C ;

Enkelmann, V ;

Mullen, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (15) :1607-1610

← 1 2 3 →