Polyfluorinated hexabenzyl hexaazaisowurtzitanes

A study of the reactivity of polyfluorobenzylamines towards the condensation with glyoxal is described. Selected fluorobenzylamines, 3,4-difluorobenzylamine, 3,4,5-trifluorobenzylamine and pentafluorobenzylamine react to give the corresponding hexabenzyl substituted hexaazaisowurtzitanes, (3,4-C6F2H3CH2)6(NCH)6 (1), (3,4,5-C6F3H2CH2)6(NCH)6 (2) and (C6F5CH2)6(NCH)6 (3). An unusual by-product is formed and could be isolated from the condensation with pentafluorobenzylamine. The exact constitution, a novel mixed O/N containing isowurtzitane, (C6F5CH2)5(NCH)5OCH (4), was elucidated by crystal structure determination. Furthermore, the crystal structures of 1 and 3 were determined.