Rearrangement reactions involving hydride and methyl anion migrations are observed when certain enolate ions derived from isopropyl and t- butyl ketones are subjected to collisional activation. For example (i) -CH2CO-i-C3H7 → -(CH2CHO)+C3H6 and (ii) -CH2CO-t-C4H9 → -(CH2COCH3)+C3H6The mechanisms of these and related reactions have been investigated by denterium labelling and product ion studies.

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Deprotonated phenyl ethylene glycols, on collisional activation, lose water by a negative ion pinacol rearrangement involving phenyl migration. For example, deprotonated benzpinacol undergoes the following reaction:Ph,C(OH)C(O-)Ph, + (PhCOCPh, -HI-+ H,O. It is proposed that this rearrangement proceeds from an eclipsed (or near eclipsed) conformer which is stabilized by the HO and 0groups forming a strong intramolecular hydrogen bond.

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