Nucleophilic substitution reactions of adamantane derivatives with cyclophosphazenes

In the present work, the reactions of cyclophosphazenes with adamantane derivatives have been investigated. The geminal-bis- (3) and geminal-tetrakis- (4) compounds have been synthesized from the reaction of hexachloro-cyclotriphosphazatriene with 1-adamantanethiol. 2-(1′-Adamantylamino)-2,4,4,6,6-pentachlorocyclotriphosphazatriene (5) has been obtained from the reaction of hexachloro-cyclotriphosphazatriene with 1-adamantylamine. Furthermore, mono- (6) and non-geminal bis-substituted 1-adamantylamino cyclotetraphosphazene compounds 7 (2-trans-6) and 8 (2-cis-4) have been isolated from the reaction of octachlorocyclotetraphosphazatetraene with 1-adamantylamine. All compounds have been fully characterized by elemental analysis, mass, 1H and 31P NMR spectroscopies. Molecular and crystal structures of 3 and 5–7 have been determined by X-ray crystallography. Compounds 3 and 4 are reported as the first examples for adamantylthio derivatives of cyclophosphazene in the literature. Compounds 5–8 have been also reported for the first time.

In this work is shown that synthesis and characterization of a series of cyclophosphazene compounds containing adamantane derivatives have been report for the first time.Figure optionsDownload as PowerPoint slideHighlights
► New cyclophosphazene compounds containing adamantane derivatives have been synthesized.
► Each of compounds has been fully characterization by spectroscopic techniques.
► Crystal structures of some products have been characterized by X-ray crystallography.