The stable anion [CCBO](-) may be formed in the chemical ionization source of a mass spectrometer by the process F- + (CH3)(3)Si-CdropC-B(O-iso-Pr)(2) --> [CCBO](-) + (CH3)(3)SiF + CH3-CH=CH2. Anion [CCBO](-) may be converted to stable doublet CCBO by a collision-induced vertical Franck-Condon oxidation in the first of two collision cells. Calculations at the MP4SDTQ/aug-cc-pVTZ//MP2(full)/6-31G(d) level of theory indicate that [CCBO]- and CCBO are linear species, with structures approximated by valence bond forms [:C=C=B=O](-) and .CdropC-B=O, respectively. Neutral CCBO may be converted to [CCBO](+) in the second collision cell by vertical ionization. Some of the [CCBO](+) cations are stable, while others are energized and undergo rearrangement to [OCCB](+). This exothermic rearrangement may occur for both the singlet and triplet forms of [CCBO](+) (the triplet form is lower in energy by only 5.2 kcal mol(-1)) with both rearrangements proceeding through distorted rhombic forms of [cyclo-CCBO](+).