Mass spectrometry in structural and stereochemical problems—CXCVII: Electron-impact induced functional group interaction in 4-benzyloxycyclohexyl trimethylsilyl ether

Abstract

There has been much interest recently in both electron-impact induced remote functional group interaction and migration of the trimethylsilyl moiety. The title compound illustrates these phenomena, showing an important (at 12 eV) peak at mass 179 which incorporates both functionalities. Moreover, the cis and trans stereoisomers show a marked difference in the relative intensity (Rel. int.) of this peak, indicating that stereochemical integrity is maintained after initial ionization. The origin of all characteristic peaks has been demonstrated using specifically labeled isotopic analogs, high resolution measurements and metastable defocusing.