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

Gruter GJM, vanBaar BLM, Gerrits TJ, Akkerman OS, Bickelhaupt F, Barkow A, Kuck D (1996)
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 (5): 925-932.

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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 [C15H12H12](.+) 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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Gruter GJM, vanBaar BLM, Gerrits TJ, et al. The remarkable electron impact mass spectrum of (2-benzyl-1,3-xylylene)-15-crown-4: Expulsion of triethylene glycol by double hydrogen transfer. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2. 1996;(5):925-932.
Gruter, G. J. M., vanBaar, B. L. M., Gerrits, T. J., Akkerman, O. S., Bickelhaupt, F., Barkow, A., & Kuck, D. (1996). The remarkable electron impact mass spectrum of (2-benzyl-1,3-xylylene)-15-crown-4: Expulsion of triethylene glycol by double hydrogen transfer. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2(5), 925-932. doi:10.1039/p29960000925
Gruter, G. J. M., vanBaar, B. L. M., Gerrits, T. J., Akkerman, O. S., Bickelhaupt, F., Barkow, A., and Kuck, D. (1996). The remarkable electron impact mass spectrum of (2-benzyl-1,3-xylylene)-15-crown-4: Expulsion of triethylene glycol by double hydrogen transfer. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 925-932.
Gruter, G.J.M., et al., 1996. The remarkable electron impact mass spectrum of (2-benzyl-1,3-xylylene)-15-crown-4: Expulsion of triethylene glycol by double hydrogen transfer. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, (5), p 925-932.
G.J.M. Gruter, et al., “The remarkable electron impact mass spectrum of (2-benzyl-1,3-xylylene)-15-crown-4: Expulsion of triethylene glycol by double hydrogen transfer”, JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, pp. 925-932.
Gruter, G.J.M., vanBaar, B.L.M., Gerrits, T.J., Akkerman, O.S., Bickelhaupt, F., Barkow, A., Kuck, D.: The remarkable electron impact mass spectrum of (2-benzyl-1,3-xylylene)-15-crown-4: Expulsion of triethylene glycol by double hydrogen transfer. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2. 925-932 (1996).
Gruter, GJM, vanBaar, BLM, Gerrits, TJ, Akkerman, OS, Bickelhaupt, F, Barkow, A, and Kuck, Dietmar. “The remarkable electron impact mass spectrum of (2-benzyl-1,3-xylylene)-15-crown-4: Expulsion of triethylene glycol by double hydrogen transfer”. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 5 (1996): 925-932.
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