4-Azabicyclo [5, 2, 2] undeca-8, 10-dien-3-ones. Photochemical Formations and Novel Rearrangements

Water soluble novel compounds, 4-azabicyclo [5, 2, 2] undeca-8, 10-dien-3-ones were synthesized on the photolysis of N-chloroacetyl derivatives of para methoxyphenethylamines (I and II). Some reactions of 4-azabicyclo [5, 2, 2] undeca-8, 10-dien-3-ones (IV, VIII and IX) in acids were examined. Compounds IV and IX bearing one and two enolether groups respectively were rearranged by hydrogen chloride treatments into 4-azatricyclo [5, 2, 2, 04, 10] undeca-8-en-3-ones (XIII, XXVI, XXVII and XXVIII). On heating of IV or IX in acetic acid, a novel fragmentation reaction took place to yield a aromatized compound, X or XXIV. On the other hand, VIII having no enol-ether group was stable to acid treatments.