PHOSPHORUS DERIVATIVES OF SPERMINE

The reaction of spermine with aromatic aldehyde leads to an equilibrat ed system between the bis imine form 1' and the hexahydropyrimidine fo rm 1. In contrary the formaldehyde adduct of spermine exist only on th e hexahydropyrimidine form 9. 1-1' is readily hydrolyzed by HCl with r egeneration of the aldehyde and spermine. The NaBH4 reduction of 1-1' leads to the dibenzyl spermine 8 and the phosphonate adducts 2 or 6 ar e obtained from 1-1' and a hydrogen phosphonate. These last two reacti ons failed with 9. Inversely 9 and 1-1' reacts equably well with tetra methyl chloro dioxaphospholane with formation of cyclic phosphinamidat es 10 and 5. In the second case a kinetic intermediate 3 can be observ ed by P-31 NMR.