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

[11] FORMATION ENTHALPY OF CORANNULENE - MICROBOMB COMBUSTION CALORIMETRY [J].

KIYOBAYASHI, T ;

NAGANO, Y ;

SAKIYAMA, M ;

YAMAMOTO, K ;

CHENG, PC ;

SCOTT, LT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (11) :3270-3271

[12] Corannulene synthesis via the pyrolysis of silyl vinyl ethers [J].

Liu, CZ ;

Rabideau, PW .

TETRAHEDRON LETTERS, 1996, 37 (20) :3437-3440

[13] Synthetic studies directed towards bucky-balls and bucky-bowls [J].

Mehta, G ;

Rao, HSP .

TETRAHEDRON, 1998, 54 (44) :13325-13370

[14] A new synthesis of corannulene [J].

Mehta, G ;

Panda, G .

TETRAHEDRON LETTERS, 1997, 38 (12) :2145-2148

[15]

MEHTA G, 1997, ADV STR ORG, V6, P139

[16]

MURRAY RW, 1960, TETRAHEDRON LETT, V7, P27

[17] Buckybowls: Polynuclear aromatic hydrocarbons related to the buckminsterfullerene surface [J].

Rabideau, PW ;

Sygula, A .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (05) :235-242

[18]

RAI AK, 1996, BOSTON COLL

[19]

SCOTT L, UNPUB

[20] CORANNULENE BOWL-TO-BOWL INVERSION IS RAPID AT ROOM-TEMPERATURE [J].

SCOTT, LT ;

HASHEMI, MM ;

BRATCHER, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1920-1921

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