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学科主题: 分析化学
题名: Gas Phase Decarbonylation and Cyclization Reactions of Protonated NMethyl-N-Phenylmethacrylamide and Its Derivatives Via an Amide Claisen Rearrangement
其他题名: 基于质子化的 N-Methyl-NPhenylmethacrylamide及其衍生物的氮杂claisen重排的气相脱羧环化反应
作者: Wang HY(王昊阳) ; Xu C(许楚) ; Zhu W(朱微) ; Liu GS(刘国生) ; Guo YL(郭寅龙)
通讯作者: 王昊阳 ; 郭寅龙
刊名: J. Am. Soc. Mass Spectrom.
发表日期: 2012-01-01
卷: 23, 期:12, 页:2149-2157
收录类别: SCI
部门归属: 中科院上海有机化学研究所
英文摘要: Gas phase decarbonylation and cyclization reactions of protonated N-methyl-N-phenylmethacrylamide and its derivatives (M center dot H+) were studied by electrospray ionization-tandem mass spectrometry (ESI-MS/MS). MS/MS experiments of M center dot H+ showed product ions were formed by loss of CO, which could only occur with an amide Claisen rearrangement. Mechanisms for the gas phase decarbonylation and cyclization reactions were proposed based on the accurate m/z measurements and MS/MS experiments with deuterated compounds. Theoretical computations showed the gas phase Claisen rearrangement was a major driving force for initiating gas phase decarbonylation and cyclization reactions of M center dot H+. Finally, the influence of different phenyl substituents on the gas phase Claisen rearrangement was evaluated. Electron-donating groups at the para-position of the phenyl moiety promoted the gas phase Claisen rearrangement to give a high abundance of fragment ions [M - CO + H](+). By contrast, electron-withdrawing groups on the phenyl moiety retarded the Claisen rearrangement, but gave a fragment ion at m/z 175 by loss of neutral radicals of substituents on the phenyl, and a fragment ion at m/z 160 by further loss of a methyl radical.
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/331003/28675
Appears in Collections:分析化学研究室_期刊论文

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Recommended Citation:
Wang HY,Xu C,Zhu W,et al. Gas Phase Decarbonylation and Cyclization Reactions of Protonated NMethyl-N-Phenylmethacrylamide and Its Derivatives Via an Amide Claisen Rearrangement[J]. J. Am. Soc. Mass Spectrom.,2012,23(12):2149-2157.
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