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Detection of a thermally unstable intermediate in the Wittig reaction using low-temperature liquid secondary ion and atmospheric pressure ionization mass spectrometry

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Journal of the American Society for Mass Spectrometry

Abstract

The signal of an extremely air sensitive and thermally unstable intermediate, four-membered ring oxaphosphetane in the Wittig reaction was detected for the first time at subambient temperature using liquid secondary ion mass spectrometry (LSIMS) and atmospheric pressure ionization (API) mass spectrometry. A copper probe and interface were constructed to perform LSIMS analysis at the temperature below −70 °C. A stable signal from a oxaphosphetane ion [in dry tetrahydrofolate (THF)] was obtained by LSIMS without using a viscous matrix. The signal of the oxaphosphetane was also detected using a low-temperature API source (−40 °C) connected to a reaction vessel.

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Authors and Affiliations

  1. Department of Chemistry, National Sun Yat-Sen University, 804, Kaohsiung, Taiwan

    Chin-Hsiung Wang, Min-Wen Huang, Chie-Yang Lee, Hsing-Long Chei, Jen-Pang Huang & Jentaie Shiea

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  1. Chin-Hsiung Wang
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  2. Min-Wen Huang
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  3. Chie-Yang Lee
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  4. Hsing-Long Chei
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  5. Jen-Pang Huang
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  6. Jentaie Shiea
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Correspondence to Jentaie Shiea.

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Wang, CH., Huang, MW., Lee, CY. et al. Detection of a thermally unstable intermediate in the Wittig reaction using low-temperature liquid secondary ion and atmospheric pressure ionization mass spectrometry. J Am Soc Mass Spectrom 9, 1168–1174 (1998). https://doi.org/10.1016/S1044-0305(98)00089-0

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  • DOI: https://doi.org/10.1016/S1044-0305(98)00089-0

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