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

[1] An Efficient Functionalization of [60]Fullerene. Diels-Alder Reaction Using 1,3-Butadienes Substituted with Electron-Withdrawing and Electron-Donating (Silyloxy) Groups
Ohno, M.
Azuma, T.
Kojima, S.
Shirakawa, Y.
Tetrahedron, 52 (14):
[2] The Diels-Alder Cycloaddition Reaction of Substituted Hemifullerenes with 1,3-Butadiene: Effect of Electron-Donating and Electron-Withdrawing Substituents
Mojica, Martha
Mendez, Francisco
Alonso, Julio A.
MOLECULES, 2016, 21 (02):
[3] Behaviour of selenophenes substituted with electron-withdrawing groups in polar Diels-Alder reactions
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Kneeteman, Maria
Mancini, Pedro
TETRAHEDRON LETTERS, 2007, 48 (40) : 7075 - 7078
[4] Exohedral functionalization of [60]fullerene by [4+2] cycloadditions. Diels-Alder reactions of [60]fullerene with electron rich 2,3-dioxy-substituted-1,3-butadienes
Tetrahedron, 15 (5421):
[5] THE DIELS-ALDER REACTION OF 2,3-DISULFUR-SUBSTITUTED 1,3-BUTADIENES
CHOU, SSP
SUN, DJ
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1988, 35 (06) : 437 - 442
[6] Silyl-substituted 1,3-butadienes for Diels-Alder reaction, ene reaction and allylation reaction
Zhao, Fei
Zhang, Shaoguang
Xi, Zhenfeng
CHEMICAL COMMUNICATIONS, 2011, 47 (15) : 4348 - 4357
[7] Synthesis of isoquinoline derivatives by Diels-Alder reactions of 2(1H)-pyridones having an electron-withdrawing group with methoxy-1,3-butadienes
Fujita, R
Hoshino, M
Tomisawa, H
Hongo, H
CHEMICAL & PHARMACEUTICAL BULLETIN, 2000, 48 (11) : 1814 - 1817
[8] Diels-Alder reaction of 2(1H)-pyridones having two electron-withdrawing groups with a diene
Hongo, H
Nakano, H
Matsuzaki, H
Okuyama, Y
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1998, 118 (03): : 105 - 109
[9] Exohedral functionalization of [60]fullerene by [4+2] cycloadditions. Diels-Alder reactions of [60]fullerene with electron rich 2,3-dioxy-substituted-1,3-butadienes.
TorresGarcia, G
Mattay, J
TETRAHEDRON, 1996, 52 (15) : 5421 - 5426
[10] A DIVERGENT DENOVO SYNTHESIS OF CARBOHYDRATES BASED ON AN ACCELERATED INVERSE ELECTRON DEMAND DIELS-ALDER REACTION OF 1-OXA-1,3-BUTADIENES
BOGER, DL
ROBARGE, KD
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24): : 5793 - 5796

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