COMPARATIVE MASS SPECTROMETRIC BEHAVIOR OF o-HYDROXYNITROSO DERIVATIVES OF THE QUINOLINE, ISOQUINOLINE, AND COUMARIN SERIES

Article abstract of DOI:10.1007/BF00487306

Benzo-substituted ortho-hydroxynitrosoquinoline and isoquinoline are found in the gas phase predominantly as the hydroxyimino-ortho-quinoid tautomeric form and under electron bombardment they do not undergo a second order Beckmann rearrangement.Molecular ions of 4-hydroxy-3-nitrosocarbostyryls and coumarin have almost exclusively the structure of the corresponding 2,4-dioxo-3-hydroxyiminohetarene; they also do not undergo rearrangement and decompose predominantly by retrodiene cleavage.