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学科主题: 有机化学
题名: Reactivity and reaction pathways of alkylalkoxybenzene radical cations Part 3. Effects of 2-alkyl substituents on the relative importance of ring-substitution over deprotonaiton of 2-alkyl-1,4-dimethoxybenzene radical cations
其他题名: Reactivity and reaction pathways of alkylalkoxybenzene radical cations Part 3. Effects of 2-alkyl substituents on the relative importance of ring-substitution over deprotonaiton of 2-alkyl-1,4-dimethoxybenzene radical cations
作者: Zhao Y(赵宇) ; Li W(李薇) ; Zhao CX(赵成学) ; Chen QY(陈庆云)
通讯作者: 陈庆云
刊名: Res. Chem. Intermed.
发表日期: 2000-01-01
卷: 26, 期:7-8, 页:691-704
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所元素有机化学实验室; 上海交通大学
英文摘要: One-electron oxidation of 2-alkyl-1,4-dimethoxybenzenes la-f(2-alkyl=Me,Et,I-Pr,, cy-C^3H^5CH^2, PhCH^2 and t-Bu) by 4-nitrobenzoyl peroxide 2 and pentaflurobenzoyl peroxide 3 was proved by the observation of great acceleration of decomposition of the peroxides at room temperture, thedetection of the corresponding radical cations 1+ a-f and product analysis. The product studies have discolosed that under the conditions employed (in acetonitrile at 40℃ ), the reactionpathways of the radical cations are greatly dependent on the nature of 2-alkyl substituents: Ring-4-nitrobenzoloxylation product at C^5and C^6 were obtained wxclusively in the reactions of the donors with aliphatic 2-alkyl substituents bearing at least one α-hydrogen atom, such as 1a, 1b, 1c and 1d; whereas in the case of 1e (with 2-benzyl group), both ring-substitution at C^5(4e) and C^ (5e) and deprotonation/4-nitrobenzoloxylation products 8e were isolated; from the donor without α-hydrogen atom, 1f, de-t-butylation products 12 and t-butyl 4-nitrobenzoate 13 were incorporated with ring-substitution at C^5 (4f) and C^6 (5f). Furtherore, the product distribution (4 over 5) is also affected by the bulkiness of 2-alkyl grou. For all the electron-transfer reactions, large amounts of the benzoic acid (4NO^2-C^6H^4COOH or C^6F^5COOH) were generated and trace amounts of de-methylation product (2-alkyl-1,4-benzoqinones 6) were also detected by ~1H NMR
语种: 英语
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/13540
Appears in Collections:中科院有机氟化学重点实验室_期刊论文

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Recommended Citation:
Zhao Y,Li W,Zhao CX,et al. Reactivity and reaction pathways of alkylalkoxybenzene radical cations Part 3. Effects of 2-alkyl substituents on the relative importance of ring-substitution over deprotonaiton of 2-alkyl-1,4-dimethoxybenzene radical cations[J]. Res. Chem. Intermed.,2000,26(7-8):691-704.
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