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Original Articles

PHOSPHORUS-NITROGEN COMPOUNDS. PART 69.1 THE REACTIONS OF GEMINAL TETRACHLORO-1′, 3′-PROPANEDIOXYCYCLOTRIPHOSPHAZA-TRIENE WITH PRIMARY AND SECONDARY AMINES. THE USE OF THE METHYLENE PROTONS OF THE 1′,3′-PROPANEDIOXY GROUP TO DISTINGUISH POSITIONAL AND GEOMETRIC ISOMERS

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Pages 143-156 | Received 11 May 1990, Accepted 09 Jun 1990, Published online: 23 Sep 2006
 

Abstract

From the reactions of the geminal tetrachloro-1′.3′-propanedioxycyclotriphosphazatriene, N3P3CI4-[O(CH2)3O]. with primary and secondary amines. the following derivatives have been isolated: N3P3Cl3R[O(CH2)3O]. R = NHC3H5. NC4H8. NC4H8O. NC5H10; N3P3Cl2R2(O(CH2)3O]. R = NHEt. NHC3H5. NHC6H11. NMe2. NC4H8 (3 isomers). NC4H8O, NC5H10; N3P3R4[O(CH2)3O], R = NHEt. NHC3H5, NMe3. NC4H8, NC4H8O. Their 1H, 13C and 31P n.m.r. spectra are reported. The non-equivalence of the OCH2 and/or the CCH2 protons of the 1′.3′-propanedioxy group is used to distinguish between geminal and nongeminal cis- and trans-isomers in N3P3Cl2R2[O(CH2)3O]. Primary amines give geminal bis-derivatives. secondary amines mainly nongeminal trans-isomers in N3 P3Cl2R2[O(CH2)3O], but for pyrrolidine cis- and geminal isomers were also isolated.

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