Completely regioselective, highly stereoselective syntheses of cis-bisfullerene[60] adducts of 6,13-disubstituted pentacenes

被引:51
作者
Miller, GP [1 ]
Mack, J [1 ]
机构
[1] Univ New Hampshire, Dept Chem, Durham, NH 03824 USA
关键词
D O I
10.1021/ol0064718
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
cis-Bisfullerene[60] adducts of 6,13-disubstituted pentacenes (R = Ph, 4'-hydroxymethylphenyl) are synthesized in 75% to 85% isolated yields under kinetically controlled Diels-Alder conditions. The cycloadditions are completely regioselective and highly stereoselective, with only traces of the diastereomeric trans-bisfullerene[60] adducts terming.
引用
收藏
页码:3979 / 3982
页数:4
相关论文
共 8 条
[1]   Action of Grignard reagents on certain pentacenequinones, 6,13-diphenylpentacene [J].
Allen, CFH ;
Bell, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :1253-1260
[2]   THE CRYSTAL AND MOLECULAR-STRUCTURE OF SYN-9-PHENYL-2,11-DITHIA[3,3]METACYCLOPHANE [J].
ANKER, W ;
BEVERIDGE, KA ;
BUSHNELL, GW ;
MITCHELL, RH .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (04) :661-666
[3]  
GRIBBLE GW, 1976, TETRAHEDRON LETT, P3673
[4]   Synthesis and characterization of a C-60-pentacene monoadduct [J].
Mack, J ;
Miller, GP .
FULLERENE SCIENCE AND TECHNOLOGY, 1997, 5 (03) :607-614
[5]  
MITCHELL R, 1981, TETRAHEDRON LETT, P5135
[6]   Solid-state [4+2] cycloaddition of fullerene C60 with condensed aromatics using a high-speed vibration milling technique [J].
Murata, Y ;
Kato, N ;
Fujiwara, K ;
Komatsu, K .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3483-3488
[7]  
Stewart J. J. P., 2007, REV COMPUTATIONAL CH, V1, P45, DOI DOI 10.1002/9780470125786.CH2
[8]   SEMIEMPIRICAL METHODS - CURRENT STATUS AND PERSPECTIVES [J].
THIEL, W .
TETRAHEDRON, 1988, 44 (24) :7393-7408