A Mass Spectral Investigation of Water and Acetic Acid Elimination From 1- and 2-Indan Derivatives

Article abstract of DOI:10.1002/oms.1210170905

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.