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Issue 5, 1996
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The remarkable electron impact mass spectrum of (2-benzyl-1,3-xylylene)-15-crown-4: expulsion of triethylene glycol by double hydrogen transfer

Abstract

During our investigations of the synthesis of magnesium-containing crown ethers, the mass spectral characterisation of a precursor, (2-benzyl-1,3-xylylene)-15-crown-4 (C21H26O4), leads to a surprising result: its electron-impact mass spectrum was nearly identical with that of 1-methylanthracene, C15H12. Several deuteriated analogues and other model compounds were synthesised and investigated with respect to their ionisation-induced and collision-induced mass spectroscopic behaviour. A mechanism for the fragmentation of the ions of [2-benzyl-1,3-xylylene]-15-crown-4 to a [C15H12+ species is proposed. It involves consecutive 1,5-H transfer, to generate an open-chain polyether group, cyclisation of the two aromatic moieties, to give an anthracene-type intermediate, and remote hydrogen transfer, to release the triethylene glycol neutral.

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Article type: Paper
DOI: 10.1039/P29960000925
J. Chem. Soc., Perkin Trans. 2, 1996, 925-932

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    The remarkable electron impact mass spectrum of (2-benzyl-1,3-xylylene)-15-crown-4: expulsion of triethylene glycol by double hydrogen transfer

    G. M. Gruter, B. L. M. van Baar, T. J. Gerrits, O. S. Akkerman, F. Bickelhaupt, A. Barkow and D. Kuck, J. Chem. Soc., Perkin Trans. 2, 1996, 925
    DOI: 10.1039/P29960000925

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