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Short Communication

Novel Amination of Phosphorus Diesters Promoted By Titanium Tetrakis(Diethylamide)

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Pages 383-385 | Received 01 Oct 1985, Published online: 14 Mar 2007

References

  • Reetz , M. T. , Wenderoth , B. and Peter , R. 1983 . J. Chem. Soc., Chem. Commun. , 406
  • DeBolster , M. W. G. 1983 . Topics in Phosphorus Chemistry . Interscience , 11 : 69
  • Bradley , D. C. and Gitlitz , M. H. 1969 . J. Chem. Soc. A , 980
  • Corey , E. J. and Cane , D. E. 1969 . J. Org. Chem. , 34 : 3053 (Me2N)2P(O)H was reported to be thermally unstable:, We found that (4) decomposed above 110°C
  • B.p. 80—85°C/1–1.5 mm. 1H n.m.r. (CDCl3) 1.12 (12 H, t, J 7.2 Hz, 4 × CH3); 2.99 (8 H, d of q, J Hp 11.7 Hz, J HH 7.2 Hz, 4 × CH,): 6.72 (1 H, d, J 570.4 Hz, PH). M.S., m/e 192 (M+, 40%, El). Anal. calcd. for C8H21N2OP: C, 50.0; H, 10.9; N, 14.6 Found: C, 49.9; H, 10.6; N, 14.4%. Data obtained for this product (4) were identical to those obtained for (4) prepared by an independent method.6
  • Walsh , E. N. D.A.S. . 1125425 . 1960 . Chem. Zentr., 1962, 14666; A. Zwierzak, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 1965, 13, 609
  • Nifantév , E. E. and Shilov , I. V. 1975 . J. Gen. Chem. USSR (Engl. Transl.) , 45 : 1241
  • Identified by the 1H n.m.r. and mass spectra
  • Sasse , K. 1964 . Organische Phosphorverbindungen , Vol. XII/2 , 413 Stuttgart : G. Thieme Verlag .
  • Ma , J. C. N. and Warnhoff , E. W. 1965 . Can. J. Chem. , 43 : 1849
  • Gray , M. D. M. and Smith , D. J. H. 1980 . Tetrahedron Lett. , 21 : 859 See e.g
  • Ti(IV) derivative is prerequisite for the amination reaction. We have found that phosphites (3) do not react with Et2NLi alone (except for the obvious deprotonation of (3)), and can be recovered unchanged after the aqueous work-up
  • Gorenstein , D. G. , Luxon , B. A. and Goldfield , E. M. 1980 . J. Am. Chem. Soc. , 102 : 1757

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