Ring closure synthetic strategies toward buckybowls:: benzannulation versus cyclopentannulation

被引：10

作者：

Dinadayalane, TC ^{[1
]}

Priyakumar, UD ^{[1
]}

Sastry, GN ^{[1
]}

机构：

[1] Pondicherry Univ, Dept Chem, Pondicherry 605014, India

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 2002年 / 01期

关键词：

D O I：

10.1039/b108030j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Computations were performed on idealized retrosynthetic routes towards two model buckybowl compunds, sumanene (I) and pinakene (II). Two possible paths for sumanene (I) and six for pinakene (II) were analyzed. The computational results unequivocally predict that benzannulation is a significantly easier process compared to cyclopentannulation in the ring closure strategies in both cases. The suitability of the theoretical models for obtaining reliable trends is assessed and generalizations for the synthetic strategies directed towards buckybowls and C-60 were made.

引用

页码：94 / 101

页数：8

共 36 条

[1] Nonplanar aromatic compounds. 3. A proposed new strategy for the synthesis of buckybowls. Synthesis, structure and reactions of [7]-, [8]- and [9] (2,7)pyrenophanes [J].

Bodwell, GJ ;

Fleming, JJ ;

Mannion, MR ;

Miller, DO .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (17) :5360-5370

[2] 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

[3]

Curl RF, 1997, ANGEW CHEM INT EDIT, V36, P1567

[4] GROUND-STATES OF MOLECULES .38. MNDO METHOD - APPROXIMATIONS AND PARAMETERS [J].

DEWAR, MJS ;

THIEL, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (15) :4899-4907

[5] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[6] Theoretical studies on the effect of sequential benzannulation to corannulene [J].

Dinadayalane, TC ;

Priyakumar, UD ;

Sastry, GN .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2001, 543 :1-10

[7] Synthetic strategies toward buckybowls and C60:: benzannulation is remarkably facile compared to cyclopentannulation [J].

Dinadayalane, TC ;

Sastry, GN .

TETRAHEDRON LETTERS, 2001, 42 (36) :6421-6423

[8]

DINADAYALANE TC, 2002, IN PRESS J MOL STRUC

[9] FULLERENE MODEL COMPOUNDS - BOWL-SHAPED AROMATIC-HYDROCARBONS AND CYCLOPHANE-BASED CAGE MOLECULES [J].

FAUST, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (13-14) :1429-1432

[10] Proposed tennis ball and basket- and -lid routes to C60:: two relevant C45 compounds [J].

Ferrier, RJ ;

Holden, SG ;

Gladkikh, O .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (20) :3505-3512

← 1 2 3 4 →