Abstract
In here, a systematic study on regioisomer selectivity in the nucleophilic substitution reactions of the cyclotriphosphazene and some its derivatives, N3P3Cl4R2 [R2 = Cl (1a); (OCH2(CF2)2CH2O) (1b); (OCH2CH2CH2O) (1c); NHPh (1d); (OCH2CH2CH2NH) (1e) and NHBut (1f)] with 1,3-propanediol has been performed. The compounds 1a–f were reacted with the 1,3-propanediol in THF solution at 1:1 mole ratio in the presence of two different bases, NaH and Et3N. The relative amounts of isomeric products, spiro and ansa were established quantitatively from the 31P NMR spectra of the reaction mixtures. The products were separated and characterized by elemental analysis, mass spectrometry, 1H and 31P NMR spectroscopy. Crystal structures of 2b, 3b, 2e and 2f have been characterized by X-ray crystallography. Although the amount of the ansa product decreased with the increase of the electron releasing capacity of R2 group, it formed in all the reactions in which the sodium salt of diol was used.
Published Version
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