An efficient functionalization of [60]fullerene. Diels-Alder reaction using 1,3-butadienes substituted with electron-withdrawing and electron-donating (silyloxy) groups

被引：49

作者：

Ohno, M ^{[1
]}

Azuma, T ^{[1
]}

Kojima, S ^{[1
]}

Shirakawa, Y ^{[1
]}

Eguchi, S ^{[1
]}

机构：

[1] NAGOYA UNIV, FAC ENGN, DEPT APPL ORGAN CHEM, CHIKUSA KU, NAGOYA, AICHI 46401, JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 14期

关键词：

D O I：

10.1016/0040-4020(96)00106-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder strategy was found suitable for the functionalization of C-60 using 1,3-butadienes substituted with an electron-withdrawing group as well as with an electron-donating group, giving cyclohexene-fused C-60 derivatives having ethoxycarbonyl, acetyl, cyano, phenylsulfonyl and nitro substituents. These cycloadducts were stabilized by conjugation with the substituent and no cycloreversion took place. Though the dienes are electron-deficient in nature, the HOMO (diene) - LUMO (C-60) interaction was significant as indicated by PM3 calculations. (C) 1996 Elsevier Science Ltd

引用

页码：4983 / 4994

页数：12

共 32 条

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