Mass spectrometric analyses of beta-ketolactone oligomers, macrocyclic or catenane structures?

Mass spectrometry is used to develop an analytical method for a new class of organic oligomeric material, beta-ketolactones. Three different series with varying oligomeric sizes are examined. The oligomers may form at least two different structures, a macrocyclic and a catenane ring. Fast atom bombardment coupled with Fourier transform mass spectrometry provides a rapid and convenient method that provides both molecular weight information and abundant fragment ions that are structurally relevant. All the compounds are found to work well with the mass spectrometric analysis. Electrospray ionization coupled with triple-quadrupole mass spectrometry was also evaluated and found to yield results that are similar to FAB. On the basis of the FAB and the low-energy collisionally activated dissociation spectra, we conclude that these compounds are macrocyclic rings and not catenanes.