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学科主题: 有机化学
题名: 8-Endo versus 7-exo cyclization of alpha-carbamoyl radicals. A combination of experimental and theoretical studies
其他题名: α-酰胺基自由基的8-endo与7-exo环合。实验和理论计算研究。
作者: Liu L(刘莉) ; Chen Q(陈迁) ; Wu YD(吴云东) ; Li CZ(李超忠)
通讯作者: 吴云东 ; 李超忠
刊名: J. Org. Chem.
发表日期: 2005
卷: 70, 期:5, 页:1539-1544
收录类别: SCI
部门归属: 上海有机化学研究所
英文摘要: Atom transfer radical cyclization reactions of N-(4-pentenyl)iodoacetamides were investigated. The reactions were efficiently promoted by (BF3OEt2)-O-.. For N-alkenyl-substituted iodoamides, excellent regioselectivity in favor of 8-endo cyclization was observed, while both 7-exo and 8-endo cyclization products were formed with the 8-endo cyclization preferred in the cases of N-(2-allylphenyl)substituted iodoamides. Density functional theory calculations at the B3LYP/6-31G* level revealed that both the s-trans and the s-cis conformational transition structures were feasible for the 8-endo cyclization of N-alkenyl-substituted a-carbamoyl radicals while 7-exo transition structures were much less stable. For the cyclization of N-(2-allylphenyl)-substituted alpha-carbamoyl radicals, the transition structures for 8-endo and 7-exo cyclizations were of comparable energy. These results were in excellent agreement with the experimental observations.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000227246800004
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/22808
Appears in Collections:中科院天然产物有机化学重点实验室_期刊论文

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Recommended Citation:
Liu L,Chen Q,Wu YD,et al. 8-Endo versus 7-exo cyclization of alpha-carbamoyl radicals. A combination of experimental and theoretical studies[J]. J. Org. Chem.,2005,70(5):1539-1544.
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