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学科主题: 天然产物有机化学
题名: Alkaloid-fullerens syntems trough photocycloaddition reactions
其他题名: 光环化反应生成的生物碱-富勒烯体系
作者: Guo LW(郭礼伟) ; Gao X(高翔) ; Zhang DW(张丹维) ; Wu SH(吴世晖) ; Wu HM(吴厚铭) ; Li YJ(李泳江)
通讯作者: 吴世晖
刊名: J. Org. Chem.
发表日期: 2000-01-01
卷: 65, 期:12, 页:3804-3810
收录类别: SCI
部门归属: 上海复旦大学; 中国科学院上海有机化学研究所生命有机化学实验室
英文摘要: The photocycloaddition of tertiary amines to [6O]fullerene (C^60) is an interesting and useful reaction. We wished to extend the applications of this type of reaction through an investigation of the photoaddition of alkaloids to C^60 for the purpose of synthesizing novel and complex photoadducts that are difficult to obtain by usual methods. Irradiation of tazettine (2) or gramine (3) with C^60 in toluene leads to formation of one monoadduct (6 or 7), whereas scandine (1 a) or l0-hydroxyscandine (lb) reacts with C^60 photochemically to give two products, the expected [6,6] monoadduct (5a. 5b) and a new type of monoadduct with a bis-[6, 6] closed structure (4a, 4b). These new structures were characterized by UV-vis. ET-IR, ~1H NMR, ~13C NMR, ~1H- ~1H COSY, ROESY, HMQC (heteronculear multiple-quantum coherence), and HMBC (heteronuclear multiple-bond connectivity) spectroscopy. The techniques of time-of-flight secondary ion MS (TOF-SIMS) and field desorption MS (FD-MS) were used for the mass determination. 3~He NMR analysis of the product mixture from photoaddition of la to C^60 containing a 3~He atom (3~He@C60) led to two peaks at 9.091 and- 11.090 ppm relative to gaseous 3~He, consistent with formation of a [6,6]-closed monoadduct and a bis-[6,6) closed adduct. Presumably, the bis-[6, 6] closed adducts are formed by an intramolecular [2 + 2] cycloaddition of the vinyl group to the adjacent 6,6-ring junction of C^60 after the initial photocycloaddition.
语种: 英语
相关网址: 查看原文
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/17257
Appears in Collections:上海有机化学研究所_期刊论文

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Recommended Citation:
Guo LW,Gao X,Zhang DW,et al. Alkaloid-fullerens syntems trough photocycloaddition reactions[J]. J. Org. Chem.,2000,65(12):3804-3810.
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