Geodesic polyarenes with exposed concave surfaces

被引：214

作者：

Scott, LT ^{[1
]}

Bronstein, HE ^{[1
]}

Preda, DV ^{[1
]}

Ansems, RBM ^{[1
]}

Bratcher, MS ^{[1
]}

Hagen, S ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

来源：

PURE AND APPLIED CHEMISTRY | 1999年 / 71卷 / 02期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1351/pac199971020209

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Polycyclic aromatic hydrocarbons (PAHs) in which five-membered rings have been interspersed among the six-membered rings generally display curved pi systems that can be either fully closed (fullerenes) or partially open (bowl-shaped fullerene fragments), depending on the number of five-membered rings. Both classes of compounds belong to the larger family we call 'GEODESIC POLYARENES.' Herein, we highlight the utility of high temperature aryl radical cyclizations as a general strategy for constructing strained geodesic polyarenes. We also report the first examples of reactions at the 'interior' carbon atoms of neutral PAHs that are not fullerenes, e.g. carbene additions, 1,3-dipolar cycloadditions, osmylation, nucleophilic addition of MeLi, and electrophilic addition of +CHCl2 and +CCl3.

引用

页码：209 / 219

页数：11

共 29 条

[1]

BARTH WE, 1971, J AM CHEM SOC, V93, P1730

[2] DIBENZO[GHI,MNO]FLUORANTHENE [J].

BARTH, WE ;

LAWTON, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (02) :380-&

[3] SYNTHESIS AND DYNAMICS OF THE CORANNULENE NUCLEUS [J].

BORCHARDT, A ;

FUCHICELLO, A ;

KILWAY, KV ;

BALDRIDGE, KK ;

SIEGEL, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1921-1923

[4]

BRATCHER MS, 1996, THESIS BOSTON COLL

[5]

CHENG PC, 1996, THESIS BOSTON COLL

[6] Crystallographic characterization of the molecular structure and solid state packing of the fullerene-shaped hydrocarbon C36H12 [J].

Forkey, DM ;

Attar, S ;

Noll, BC ;

Koerner, R ;

Olmstead, MM ;

Balch, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (24) :5766-5767

[7] HIGH-TEMPERATURE SYNTHESIS OF BOWL-SHAPED SUBUNITS OF FULLERENES .2. FROM 9,9'-BI-9H-FLUORENPLIDENE TO DIINDENO[1,2,3,4-DEFG-1',2',3',4'-MNOP]CHRYSENE [J].

HAGEN, S ;

NUECHTER, U ;

NUECHTER, M ;

ZIMMERMANN, G .

POLYCYCLIC AROMATIC COMPOUNDS, 1995, 4 (04) :209-217

[8] Novel syntheses of three C30H12 bowl-shaped polycyclic aromatic hydrocarbons [J].

Hagen, S ;

Bratcher, MS ;

Erickson, MS ;

Zimmermann, G ;

Scott, LT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (04) :406-408

[9] OSMYLATION OF C(70) - REACTIVITY VERSUS LOCAL CURVATURE OF THE FULLERENE SPHEROID [J].

HAWKINS, JM ;

MEYER, A ;

SOLOW, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (16) :7499-7500

[10]

JOSHI GC, 1972, SYNTH-INT J METHODS, P317

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