Mass spectra and organic analysis. Part VII. The mass spectra of the menthols, carvomenthols, their acetates and related alcohols

Abstract

The mass spectra of the saturated p-menthane alcohols are described. Fission occurs preferentially around the carbinol carbon and adjacent to the ring substituents. The tertiary alcohols lose water less readily than the secondary alcohols. Loss of methyl is appreciable in only one case (menth-1-ol). The stereochemical isomers of menthol and carvomenthol are readily distinguished by their mass spectra. The acetates of menthol and carvo-menthol behave quite differently, resembling the menthenes formed from them by loss of acetic acid in a 1,2-elimination. Many of the hypothetical fragmentations were confirmed by deuteration studies.