Phosphorus-Nitrogen Compounds: The Reactions of Hexachlorocyclotriphosphazatriene with Pentane-1,5-Diol. Nuclear Magnetic Resonance Studies of The Products

Abstract

From the reactions of hexachlorocyclotriphosphazatriene, N3P3Cl6 (1) with pentane-1,5-diol (2) in dichloromethane solution, the following derivatives have been isolated: 2,2-spiro(1,5-pentanedioxy)-4,4,6,6-tetrachlorocyclotriphosphazatriene, N3P3Cl4[O(CH2)(5)O] (3); its ansa isomer, 1,3-ansa(1,5-pentanedioxy)-1,3,5,5-tetrachlorocyclotriphosphazatriene, (4); bis spiro(1,5-pentanedioxy)-6,6-dichlorocyclotriphosphazatriene, N3P3Cl2[O(CH2)(5)O](2) (5); its spiro-ansa isomer, (1,5-pentanedioxy)-1,3-dichlorocyclotriphosphazatriene (6); as well as the bino(1,5-pentanedioxy)-di-(pentachlorocyclotriphosphazatriene), N3P3Cl5 [O(CH2)(5)O]N3P3Cl5 (7), and tri-bino(1,5-pentanedioxy)-di (trichlorocyclotriphosphazatriene), N3P3Cl3[O(CH2)(5)O](3)N3P3Cl3, (8) derivatives. Their structures were established by MS and NMR with the use of H-1, C-13, and P-31 spectroscopy. Product types and relative yields are compared with those of the previously investigated diol derivatives. The yield of the mono-ansa product (25%) obtained in this system was considerably increased relative to those of the propane-1,3-diol derivative (11.2%) and decreased relative to the 2,2-dimethyl-propane-1,3-diol (36.2%), and bis(2-hydroxyethyl) ether (34.5%) derivatives.