Chemistry of 2-Substituted Adamantanes. III. Mass Spectra of 1- and 2-Adamantanethiol, 2-Adamantanol, and 2-Adamantanamine

Abstract

The mass spectra of 1- and 2-adamantanethiol (1 and 2a), 2-adamantanol (2c), and 2-adamantanamine (2d) have been studied. The isomeric thiols give almost identical spectra and loss of the sulfhydryl radical produces the most abundant ion, while the molecular ion peaks have 9 and 21% relative intensity for 1 and 2a, respectively. Elimination of H2S is an insignificant process. In the fragmentation of 2c and d, loss of H2O and NH3 as a single group occurs (metastable peaks), giving M-H2O and M-NH3 ions, both at m/e 134; this produces the base peak for 2c and the second most intense (93%) peak for 2d. Further fragmentation of these ions results in very similar peak patterns for 2c and d. The amine shows a very intense molecular ion peak (79%) and an M-1 base peak ion. The mass spectra of 2c and d are very different from those of 1-adamantanol and 1-adamantanamine.