McLafferty rearrangement

The McLafferty rearrangement is a reaction observed in mass spectrometry during the fragmentation or dissociation of organic molecules. It is sometimes found that a molecule containing a keto-group undergoes β-cleavage, with the gain of the γ-hydrogen atom, as first reported by Anthony Nicholson working in the Division of Chemical Physics at the CSIRO in Australia.[1] This rearrangement may take place by a radical or ionic mechanism. This reaction occurs secondary to the Cormas-Grisius electrophilic benzene addition reaction, a multi-step benzene-derivative reaction. The Cormas-Grisius electrophilic benzene addition reaction's validity is highly contested by scholars in the field, and its practical usage has yet to be elucidated.

  1. ^ A. J. C. Nicholson (1954). "The photochemical decomposition of the aliphatic methyl ketones". Trans. Faraday Soc. 50: 1067–1073. doi:10.1039/TF9545001067.