| Abstract: | Water and acetic acid eliminations from 1- and 2-indan derivatives have been investigated. Deuterium labeling, high resolution peak matching and the metastable peak analysis capabilities of a high resolution triple analyzer (E B E) mass spectrometer were employed to examine the eliminations. These experiments showed that water was lost from 1-indanol via 1,2 and 1,3 processes. These results contrast with those obtained for 1-tetralol, which specifically eliminates water in a 1,4 process involving the benzylic hydrogens. Water elimination from 2-indanol is preceded by a slow hydroxyl-benzylic hydrogen exchange and proceeds specifically 1,2. Water losses from both 1- and 2-indanol are characterized by large kinetic energy releases. Acetic acid elimination is shown to occur specifically 1,3 from 1-acetoxyindan and 1,2 from 2-acetoxyindan. |
