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)5O] (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)5O]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)5O]N3P3Cl5 (7), and tri-bino(1,5-pentanedioxy)-di (trichlorocyclotriphosphazatriene), N3P3Cl3[O(CH2)5O]3N3P3Cl3, (8) derivatives. Their structures were established by MS and NMR with the use of 1H, 13C, and 31P 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.
GRAPHICAL ABSTRACT
Acknowledgments
We are grateful to Shin Nisso Co., Ltd., for a generous gift of hexachlorocyclotriphosphazatriene. We are indebted to the School of Pharmacy for mass spectrometric data obtained under the auspices of the University of London Intercollegiate Research Services. We are grateful to Dr. H. G. Parkes and Mr. D. Shipp for obtaining the NMR data.
[Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional tables and figures.]