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Original Articles

FACILE STEREOSELECTIVE SYNTHESIS OF 2H-1,2,3-DIAZA-PHOSPHOLE SPIROPHOSPHORANE DERIVATIVES

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Pages 255-259 | Received 02 Jan 1989, Accepted 15 Feb 1989, Published online: 04 Oct 2006

References

  • Schmidpeter , A. 1986 . Phosphorus and Sulfur , 28 : 71 See inter alia
  • Schmidpeter , A. , Wrackmeyer , B. and Naturforsch , Z. 1986 . B: Anorg. Chem., Org. Chem. , 41 : 553 [Chem. Abs. 1987, 107, 233961
  • Yeung Lam , Y. Y. C. Ko. , Carrie , R. , Toupet , L. and De Sarlo , F. 1986 . Bull. Soc. Chim. FR. , : 115
  • Arbuzov , B. A. , Dianova , E. N. , Galiaskarova , R. T. , Chernov , P. P. , Litvinov , I. A. and Naumov , V. A. 1987 . Z., Obschch. Khim. , 57 : 1949 [Chem. Abs. 1988, 109, 129140u].
  • Baccolini , G. and Todesco , P. E. 1974 . J. Org. Chem. , 39 : 2650
  • Baccolini , G. and Todesco , P. E. 1975 . J. Org. Chem. , 40 : 2318
  • Baccolini , G. and Todesco , P. E. 1978 . Tetrahedron Lett. , : 1891
  • Baccolini , G. , Bartoli , G. and Todesco , P. E. 1980 . Phosphorus and Sulfur , 9 : 203
  • Baccolini , G. , Dalpozzo , R. and Todesco , P. E. 1988 . J. Chem. Soc. Perkin Trans. , 1 : 971 and references cited therein.
  • Baccolini , G. and Sandali , C. 1987 . J. Chem. Soc. Chem. Comm. , : 788
  • Smith , D. J. 1979 . Comprehensive Organic Chemistry , Edited by: Barton , Sir D. H. and Ollis , W. D. Vol. 2 , Oxford : Pergamon Press . ch. 10.
  • Luckenbach , R. 1973 . “ Dynamic Stereochemistry of Pentaco-ordinated Phosphorus and Related Elements ” . Stuttgart : George Thieme-Verlag .
  • McEwen , W. E. and Berlin , K. D. , eds. 1975 . Dowden , Stroudsbourg , Pa. : Hutchinson and Ross . parts I and II, Organophosphorus Stereochemistry
  • Sheldrick , W. S. 1978 . Topics in Current Chemistry , Vol. 73 , 1 New York : Springer-Verlag .
  • Baccolini , G. , Dalpozzo , R. , Mele , V. and Mezzina , E. 1988 . Phosphorus and Sulfur , 39 : 179 Acidic conditions and polar solvents favour decomposition of adduct [A] to indole.
  • The prefixes cis and trans refer to the relationship between the P-Ph and C,-Ph groups.
  • Baccolini , G. , Spagnolo , P. and Todesco , P. E. 1980 . Phosphorus and Sulfur , 8 : 127
  • C33H28N3OP, M = 513.58, Monoclinic, space group P21/2, a = 13.167 (3). B = 17.738 (5). c = 11.694 (3) Å, β = 95.81 (1)°, Z = 4, Dc = 1.25g/cm3. A total of 5193 reflections were collected on a Philips PW 1100 difractometer, using MoKα radiations (λ = 0.7107 Å). The structure was solved by direct methods and refined by isotropic least squares methods to an agreement factor of 0.072. SHELX and PLUTO programs were used. Selected bond lengths (Å) and angles (7deg;): P-N1 1.671(6), P–N2 1.824(6), P—C1 1.867(8), P—C2 1.845(5), P-O 1.740(5); N2–P—C1 85.4(3), N2–P–C2, 94.5(2), N2–P–N1 89.9(3), C1–P—C2 111.3(3), C2–P–N1 123.4(4). C1–P–N1 125.3(3), O–P–C1 92.3(3), O– P-C2 90.0(2). O–P–N1 88.1(3) (Baccolini G., Foresti E., Pradella G., loint ltalo-Swiss Meeting on Crystallography, Crystal Growth and Material Sciences, Trento, Italy, 1980, p. 123).
  • von Itzstein , M. and Jenkins , I. D. 1986 . J. Chem. Soc Perkin Trans , 1 : 437
  • Majoral , J. P. , Kraemer , R. , N'gando , T. and M'pondo . 1980 . J. Navech, Tetrahedron Lett , 21 : 1307
  • Navech , J. , Kraemer , R. and Majoral , J. P. 1980 . Tetrahedron Left , 21 : 1449
  • Goncalves , H. , Dormoy , J. R. , Chapleur , Y. , Castro , B. , Fauduet , H. and Burgada , R. 1980 . Phosphorus and Sulfur , 8 : 147
  • Both forms were previously detected. For example see ref. 6a (betainic intermediate) and ref. 6b (pentaco-ordinate one).
  • Baccolini , G. , Foresti , E. and Krajewsky , A. 1979 . J. Chem. Soc. Perkin Trans , 1 : 893
  • Mongiorgi , R. , Pradella , G. and Baccolini , G. 1980 . Cryst. Struct. Comm. , 9 : 1089
  • Baccolini , G. , Busetto , L. , Roncarolo , A. , Albano , V. G. and Demartin , F. 1987 . J. Chem. Soc. Dalton Trans , : 21
  • Brodka and Simon , H. 1969 . Chem. Eer. , 102 : 3647

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