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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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 [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.
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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