Organocyclotriphosphazenes with poly Schiff bases and aldehydes from hexachlorocyclotriposphazene, 5-chloro-salicylaldehyde and 5-bromosalicylaldehyde under the room conditions without using Ar or N-2 atmosphere

In this study, the reactions of hexachlorocyclotriphosphazene with 5-chloro-salicylaldehyde and 5-bromo-salicylaldehyde were separately performed in the presence of K2CO3 and triethylamine as a base without using Ar or N-2 atmosphere for the preparation of the organocyclotriphosphazene derivatives bearing six formyl groups (2 and 3) again. These reactions were monitored by P-31 NMR spectroscopy to determine the formation time of the compounds (2 and 3). The result of this analysis showed that the compounds (2 and 3) occurred within 3 h under the above reaction conditions after the reactions begun. The P-31 NMR spectra of the mixtures clearly displayed only singlet signal in the range of 8-9 ppm corresponding to characteristic phosphorus signals of cyclotriphosphazenes. Moreover, these two compounds were obtained in high yields even under such mild reaction conditions. In addition, the compounds (2 and 3) were reacted with aniline and some aniline derivatives for the production of new organocyclotriphosphazene derivatives bearing poly Schiff bases (2a-2k and 3a-3k). Although all the primary amines in these reactions were used more than necessary, it was detected that the organocyclotriphosphazene derivative including both formyl and Schiff base moieties (2k and 3k) occurred from only 4-nitro-aniline. Most importantly of all, hydrolysis of hexachlorocyclotriphosphazene in THE solution was also studied. It was determined that hexachlorocyclotriphosphazene did not hydrolysis under these conditions.