Unusual cross-ring SN2 reactions of [MH]− ions of methoxyacetanilides

Blanksby, S.J., Dua, S., & Bowie, J.H. (1995) Unusual cross-ring SN2 reactions of [MH]− ions of methoxyacetanilides. Rapid Communications in Mass Spectrometry, 9(2), pp. 177-179.

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Deprotonated o, m-, and p-methoxyacetanilide show pronounced peaks in their collision-induced tandem mass spectra (MS/MS) produced by losses of the elements of C2H6. It is proposed that this reaction is a 'cross-ring' internal S(N)2 reaction involving an incipient methyl anion. For example, p-CH3O-C6H4-N--CO-CH3--> [(p.CH3O-C6H4-N=C=O)CH3-]--> O---C6H4-N=C=O+C2H6.

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ID Code: 70656
Item Type: Journal Article
Refereed: Yes
Keywords: collision-induced dissociations, gas-phase
DOI: 10.1002/rcm.1290090214
ISSN: 0951-4198
Divisions: Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 29 Apr 2014 03:45
Last Modified: 29 Apr 2014 03:45

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