81726-57-0Relevant articles and documents
1,3-DIPOLAR CYCLOADDITIONS OF AROMATIC AZOXY COMPOUNDS TO STRAINED CYCLOALKANES
Huisgen, Rolf,Gambra, Francisco Palacios
, p. 55 - 58 (2007/10/02)
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.
1,3-Dipolar Cycloadditions, 86. Aromatic Azoxy Compounds and Strained Cycloalkenes
Huisgen, Rolf,Gambra, Francisco Palacios
, p. 2242 - 2255 (2007/10/02)
4,4'-Dicyano- and 4,4'-dinitroazoxybenzene as well as benzocinnoline N-oxide combine with (E)-cyclooctene or (1E,5Z)-1,5-cyclooctadiene to give bicyclic 1,2,3-oxadiazolidines which undergo in situ 1,3-dipolar cycloreversion with opening of both rings.Azomethine imines are formed which are connected by a hexamethylene chain with an aldehyde function.These new 1,3-dipoles add to a second molecule of the strained cycloalkene and furnish derivatives of cyclooctapyrazole as 1:2 adducts in high yields.A 1,4 H-shift of the intermediate azomethine imine competes at low concentration of the (E)-cyclooctene and produces an 8-hydrazino-7-octenal as a 1:1 product.
