Cycloadditions between carbonyl oxides and dicarbonyl compounds: isolation and characterisation of novel polycyclic 1,2,4,6-tetroxepane derivatives

摘要: Formaldehyde O-oxide reacts with dicarbonyl compounds to produce mono-ozonides formed by conventional [3 + 2] cycloadditions an aldehydic carbonyl group of the substrate, and/or polycyclic 1,2,4,6-tetroxepane derivatives arising from formal 2 involving both groups. Similar reactions between more highly substituted oxides, benzaldehyde and octanal O-oxides, yielded corresponding monoozonides as sole isolable cycloaddition products. In certain favourable cases, could undergo acid-catalysed intramolecular rearrangement 1,2,4,6-tetroxepanes. X-Ray crystallographic analyses two 1,2,4,6-tetroxepanes, 6a 13b, are recorded.