Octaphenylnaphthalene and decaphenylanthracene

被引：123

作者：

Qiao, XX ^{[1
]}

Padula, MA ^{[1
]}

Ho, DM ^{[1
]}

Vogelaar, NJ ^{[1
]}

Schutt, CE ^{[1
]}

Pascal, RA ^{[1
]}

机构：

[1] PRINCETON UNIV,DEPT CHEM,PRINCETON,NJ 08544

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1996年 / 118卷 / 04期

关键词：

D O I：

10.1021/ja953669s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Octaphenylnaphthalene (2) was synthesized by the addition of tetraphenylbenzyne to tetraphenylcyclopentadienone, and decaphenylanthracene (3) was synthesized by the addition of the same aryne to hexaphenylisobenzofuran followed by deoxygenation of the adduct. The structures of both compounds were determined by X-ray analysis. Compound 2 adopts a conformation of approximate C-i symmetry with a slightly undulating naphthalene nucleus, but compound 3 exhibits C-2 (and approximate D-2) symmetry with a 63 degrees twist of the central anthracene.

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页码：741 / 745

页数：5

相关论文

共 24 条

[1] THE 1ST SYNTHESIS OF OCTAKIS(ARYLTHIO)NAPHTHALENES - AN X-RAY STUDY OF A NOVEL PRESSURE-INDUCED COLOR AND CONFORMATIONAL CHANGE IN CRYSTALLINE OCTAKIS(PHENYLTHIO)NAPHTHALENE [J].

BARBOUR, RH ;

FREER, AA ;

MACNICOL, DD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (07) :362-363

[2] CRYSTAL STRUCTURE OF A MODIFICATION OF HEXAPHENYLBENZENE [J].

BART, JCJ .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1968, B 24 :1277-&

[3] REARRANGEMENT + CLEAVAGE OF 2-ARYLIODONIOBENZOATES - TRAPPING AGENTS FOR BENZYNE [J].

BERINGER, FM ;

HUANG, SJ .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (02) :445-&

[4]

BRADY JH, 1982, J CHEM RES, P1541

[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]

DILTHEY W, 1933, CHEM BER, V66, P1627

[7] DISAPPEARING POLYMORPHS [J].

DUNITZ, JD ;

BERNSTEIN, J .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (04) :193-200

[8] SYNTHESIS OF PHENYLATED PHTHALIMIDES - DIELS-ALDER REACTION OF TETRAPHENYLCYCLOPENTADIENONE WITH MALEIMIDES [J].

HARRIS, FW ;

NORRIS, SO .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1972, 9 (06) :1251-1253

[9] DEOXYGENATION OF ARENE 1,4-ENDOXIDES WITH LOW-VALENT METALS [J].

HART, H ;

NWOKOGU, G .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (07) :1251-1255

[10] CRYSTAL AND MOLECULAR-STRUCTURES OF OVERCROWDED HALOGENATED COMPOUNDS .8. 2 OVERCROWDED NAPHTHALENES - OCTACHLORONAPHTHALENE AND TETRABENZNAPHTHALENE (DIBENZO[G,P]CHRYSENE) [J].

HERBSTEIN, FH .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1979, 35 (JUL) :1661-1670