Mass spectra and organic analysis. Part VIII. The mass spectra of piperitone, the piperitols, and related products

Abstract

With the aid of deuteriation studies and exact mass measurements, structures for the ions observed in the mass spectra of piperitone and cis- and trans-piperitol are given, and related to the simpler 3-methylcyclohexenone and 3-methylcyclohexenol. Keto–enol interconversion within the mass spectrometer are shown to be unlikely. The loss of methyl attached to a double bond in the 3-methylcyclohexenols is described. The piperitol spectra are highly dependent on the condition of the mass spectrometer so far as the loss of water is concerned.