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. Author manuscript; available in PMC: 2012 Feb 24.
Published in final edited form as: J Am Soc Mass Spectrom. 2011 Jul 13;22(9):1534–1551. doi: 10.1007/s13361-011-0185-x

Scheme 2.

Scheme 2

Proposed fragmentation mechanism of 9-NO2-OA. The fragmentation proceeds through a series of steps that include rearrangement, 1,3-cycloaddition and a final retro-1,3-fragmentation to a nitrile and corresponding unsaturated aldehyde. Sidebar: potential rearrangement of nitro group to hypothesized peroxynitroso intermediate