1,3-DIPOLAR CYCLOADDITIONS OF AROMATIC AZOXY COMPOUNDS TO STRAINED CYCLOALKANES

Article abstract of DOI:10.1016/S0040-4039(00)97530-0

The 1,2,3-oxadiazolidines resulting from the addition of 4,4'-dicyanoazoxybenzene to trans-cyclooctene or cis,trans-cycloocta-1,5-diene are not stable, but suffer 1,3-dipolar cycloreversion to give an azomethine imine; this intermediate is either captured by a second molecule of the starined cycloalkene to give 1:2 adducts in high yields ot it tautomerizes to an enehydrazine. 4,4-Dinitroazoxybenzene and benzocinnoline N-oxide react analogously.