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      Reactivity, structure and electrospray mass spectrometry of pentafluoro- and pentachloro-phenoxy-substituted cyclotriphosphazenes

      Depree, Craig V.; Ainscough, Eric W.; Brodie, Andrew M.; Burrell, Anthony K.; Lensink, Cornelis; Nicholson, Brian K.
      DOI
       10.1016/S0277-5387(00)00511-8
      Link
       www.sciencedirect.com.ezproxy.waikato.ac.nz:2048
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      Depree, C.V., Ainscough, E.W., Brodie, A.M., Burrell, A.K., Lensink, C. & Nicholson, B.K. (2000). Reactivity, structure and electrospray mass spectrometry of pentafluoro- and pentachloro-phenoxy substituted cyclotriphosphazenes. Polyhedron, 19(18-19), 2101-2110.
      Permanent Research Commons link: https://hdl.handle.net/10289/209
      Abstract
      The reaction of N3P3Cl6 with the sodium salts of pentachloro- and pentafluorophenol, has been investigated. In contrast to the non-geminal substitution typified by other RO− nucleophiles, the regiochemistry of the reaction of C6X5O− (X=Cl and F) with N3P3Cl6 is dominated by geminal substitution. The reaction of C6Cl5O− with N3P3Cl6 in refluxing tetrahydrofuran yielded gem-N3P3Cl2(OC6Cl5)4 (1) as the major product. The fully substituted derivative N3P3(OC6Cl5)6 (2) was attained in low yield from reaction in refluxing diglyme. In contrast, the reaction of C6F5O− with N3P3Cl6 in refluxing tetrahydrofuran yielded the fully substituted product N3P3(OC6F5)6 (3) after approximately 4 h. 31P NMR spectral results suggest the C6F5O− ion may be attacking in a 'random' fashion at low degrees of substitution, which is largely replaced by an electronic geminal-directing effect at tetrasubstitution. Single crystal X-ray crystallographic analyses have been carried out on compounds 1 and 3. Electrospray mass spectrometry has been evaluated as a general technique for characterizing cyclotriphosphazenes, N3P3R6. If R=OEt or OPh, good positive ion spectra are observed but, in contrast, if R is more strongly electron withdrawing (Cl, C6Cl5O or C6F5O) negative ion spectra are obtained.
      Date
      2000-09-01
      Type
      Journal Article
      Rights
      This article is published in the journal Polyhedron, (c) 2000 Elsevier Science Ltd.
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      • Science and Engineering Papers [3122]
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