Metastable Decompositions of Cyclopentanol Ions and +. Ions with the Oxygen on the First Carbon

Article abstract of DOI:10.1002/oms.1210190102

Ionized cyclopentanol and ^+. ions with the oxygen on the first carbon lose methyl, ethylene, ethyl ethane and water in their metastable decompositions.We show by collisionally activated decompositions of the products that the losses of ethyl form CH3CH2CO⁺, the losses of ethylene form CH3C^.HCH=O⁺H, and the losses of methyl probably yield CH3C(=O⁺H)CH=CH2.Deuterium labeling indicates that ethyl loss from ionized cyclopentanol occurs following α-cleavage of the ring, isomerization to the enol isomer of ionized n-pentanal and subsequent isomerization to the 3-pentanone ion.