REACTION OF C-60 WITH BENZOCYCLOBUTENOL - EXPEDITIOUS ROUTE TO FULLERENE ADDUCTS

被引：86

作者：

ZHANG, XJ ^{[1
]}

FOOTE, CS ^{[1
]}

机构：

[1] UNIV CALIF LOS ANGELES,DEPT CHEM & BIOCHEM,LOS ANGELES,CA 90024

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 18期

关键词：

D O I：

10.1021/jo00097a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of C-60 with benzocyclobutenol (2a) and its methoxy ether (2b) in refluxing toluene gave 1,9-dihydrofullerene cycloadducts a and 3b in 59% and 50% yields, respectively. The alcohol was converted to pyranyl ether (4), acrylate (5), p-vinylbenzoate (6) and acid succinate esters (7) in good yields under very mild conditions. The adducts exist as two interconverting boat conformers. Acrylate 5 and p-vinylbenzoate 6 should be useful for polymerization studies. Acid 7 shows enhanced solubility in polar solvents.

引用

页码：5235 / 5238

页数：4

共 45 条

[1] METALATION OF ORTHO-HALOSTYRENE OXIDES - PREPARATION OF BENZOCYCLOBUTENOLS [J].

AKGUN, E ;

GLINSKI, MB ;

DHAWAN, KL ;

DURST, T .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (13) :2730-2734

[2] 2 DIFFERENT FULLERENES HAVE THE SAME CYCLIC VOLTAMMETRY [J].

ALLEMAND, PM ;

KOCH, A ;

WUDL, F ;

RUBIN, Y ;

DIEDERICH, F ;

ALVAREZ, MM ;

ANZ, SJ ;

WHETTEN, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1050-1051

[3] SYNTHESIS OF ALPHA-AMINO-ACID DERIVATIVES OF C-60 FROM 1,9-(4-HYDROXYCYCLOHEXANO)-BUCKMINSTERFULLERENE [J].

AN, YZ ;

ANDERSON, JL ;

RUBIN, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) :4799-4801

[4]

ANDERSON JE, IN PRESS J AM CHEM S

[5] ON THE POTENTIAL-ENERGY SURFACE FOR RING INVERSION IN CYCLOHEXENE AND RELATED MOLECULES [J].

ANET, FAL ;

FREEDBERG, DI ;

STORER, JW ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10969-10971

[6] PHOTOPHYSICAL PROPERTIES OF C60 [J].

ARBOGAST, JW ;

DARMANYAN, AP ;

FOOTE, CS ;

RUBIN, Y ;

DIEDERICH, FN ;

ALVAREZ, MM ;

ANZ, SJ ;

WHETTEN, RL .

JOURNAL OF PHYSICAL CHEMISTRY, 1991, 95 (01) :11-12

[7] ELECTRON-TRANSFER TO TRIPLET C-60 [J].

ARBOGAST, JW ;

FOOTE, CS ;

KAO, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2277-2279

[8] PHOTOCHEMICAL REACTIONS .3. THERMAL GENERATION OF PHOTOENOLS AND THEIR DERIVATIVES FROM SUBSTITUTED 1,2-DIHYDROBENZOCYCLOBUTENES [J].

ARNOLD, BJ ;

SAMMES, PG ;

WALLACE, TW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (03) :409-414

[9]

BELIK P, 1993, ANGEW CHEM INT EDIT, V32, P780

[10] ORTHOQUINODIMETHANES [J].

CHARLTON, JL ;

ALAUDDIN, MM .

TETRAHEDRON, 1987, 43 (13) :2873-2889

← 1 2 3 4 5 →