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Gas-phase fluorine migration reactions in the radical cations of pentafluorosulfanylbenzene (Aryl-SF5) and benzenesulfonyl fluoride (Aryl-SO2F) derivatives and in the 2,5-xylylfluoroiodonium ion
Alternative TitleAryl-SF5和Aryl-SO2F衍生物的自由基阳离子以及2,5-xylylfluoroiodonium离子气相氟迁移反应的研究
Gao Y(高瑛); Wang HY(王昊阳); Zhang X(张祥); Cheng JS(程家顺); Zhang F(张芳); Guo YL(郭寅龙)
2014
Source PublicationJ. Mass Spectrom.
Volume49Issue:6Pages:481-489
AbstractThe gas-phase reactions of Aryl-SF5+ and Aryl-SO2F+ have been studied with the electron ionization tandem mass spectrometry. Such reactions involve F-atom migration from the S-atom to the aryl group affording the product ion Aryl-F+ by subsequent expulsion of SF4 or SO2, respectively. Especially, the 4-pentafluorosulfanylphenyl cation 4-SF5C6H4+ (m/z 203) from 4-NO2C6H4SF5+ by loss of NO2 could occur multiple F-atom migration reactions to the product ion C6H4F3+ (m/z 133) by loss of SF2 in the MS/MS process. The gas-phase reactions of 2,5-xylylfluoroiodonium (pXyl-I+F, m/z 251) have also been studied using the electrospray tandem mass spectrometry, which involve a similar F-atom migration process from the I-atom to the aryl group giving the radical cation of 2-fluoro-p-xylene (or its isomer 4-fluoro-m-xylene, m/z 124) by reductive elimination of an iodine atom. All these gas-phase F-atom migration reactions from the heteroatom to the aryl group led to the aryl-F coupling product ions with a new formed CAryl-F bond. Density functional theory calculations were performed to shed light on the mechanisms of these reactions. Copyright (c) 2014 John Wiley & Sons, Ltd.
Subject Area分析化学
DOI10.1002/jms.3363
URL查看原文
Indexed BySCI
Language英语
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Cited Times:4[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/38594
Collection分析化学研究室
Corresponding AuthorWang HY(王昊阳); Guo YL(郭寅龙)
Affiliation中科院上海有机化学研究所
Recommended Citation
GB/T 7714
Gao Y,Wang HY,Zhang X,et al. Gas-phase fluorine migration reactions in the radical cations of pentafluorosulfanylbenzene (Aryl-SF5) and benzenesulfonyl fluoride (Aryl-SO2F) derivatives and in the 2,5-xylylfluoroiodonium ion[J]. J. Mass Spectrom.,2014,49(6):481-489.
APA 高瑛,王昊阳,张祥,程家顺,张芳,&郭寅龙.(2014).Gas-phase fluorine migration reactions in the radical cations of pentafluorosulfanylbenzene (Aryl-SF5) and benzenesulfonyl fluoride (Aryl-SO2F) derivatives and in the 2,5-xylylfluoroiodonium ion.J. Mass Spectrom.,49(6),481-489.
MLA 高瑛,et al."Gas-phase fluorine migration reactions in the radical cations of pentafluorosulfanylbenzene (Aryl-SF5) and benzenesulfonyl fluoride (Aryl-SO2F) derivatives and in the 2,5-xylylfluoroiodonium ion".J. Mass Spectrom. 49.6(2014):481-489.
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