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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
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)
2000
发表期刊J. Org. Chem.
ISSN0022-3263
卷号65期号:12页码:3804-3810
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.
学科领域天然产物有机化学
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
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收录类别SCI
语种英语
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/17257
专题上海有机化学研究所
通讯作者Wu SH(吴世晖)
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GB/T 7714
Guo LW,Gao X,Zhang DW,et al. Alkaloid-fullerens syntems trough photocycloaddition reactions[J]. J. Org. Chem.,2000,65(12):3804-3810.
APA 郭礼伟,高翔,张丹维,吴世晖,吴厚铭,&李泳江.(2000).Alkaloid-fullerens syntems trough photocycloaddition reactions.J. Org. Chem.,65(12),3804-3810.
MLA 郭礼伟,et al."Alkaloid-fullerens syntems trough photocycloaddition reactions".J. Org. Chem. 65.12(2000):3804-3810.
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