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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

12 Issues per year


IMPACT FACTOR 2016: 0.631

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1865-7117
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Volume 50, Issue 12 (Dec 1995)

Issues

Zur Chemie der 1,3,5-Triaza-2-phosphorinan-4,6-dione. Teil IX. Umsetzungen einiger 1,3,5-Triorgano-1,3,5-triaza-2λ3-phosphorinan-4,6-dione mit Hexafluoraceton / Chemistry of the 1,3,5-Triaza-2-phosphorinan-4,6-diones. Part IX. Reaction of some 1,3,5-Triorgano-1,3,5-triaza-2λ3-phosphorinan-4,6-diones with Hexafluoroacetone

Ion Neda
  • Institut für Anorganische und Analytische Chemie der Technischen Universität. Postfach 3329, D-38023 Braunschweig
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Michael Farkens
  • Institut für Anorganische und Analytische Chemie der Technischen Universität. Postfach 3329, D-38023 Braunschweig
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Axel K. Fischer
  • Institut für Anorganische und Analytische Chemie der Technischen Universität. Postfach 3329, D-38023 Braunschweig
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Peter G. Jones
  • Institut für Anorganische und Analytische Chemie der Technischen Universität. Postfach 3329, D-38023 Braunschweig
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  • De Gruyter OnlineGoogle Scholar
/ Reinhard Schmutzler
  • Institut für Anorganische und Analytische Chemie der Technischen Universität. Postfach 3329, D-38023 Braunschweig
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Published Online: 2014-06-02 | DOI: https://doi.org/10.1515/znb-1995-1203

The reactions of 2-(2-chloroethyl)amino-1,5-dimethyl-3-phenyl-1,3,5-triaza-2λ3-phosphorinan- 4,6-dione (1), 2-bis(2-chloroethyl)amino-1,5-dimethyl-3-phenyl-1,3,5-triaza-2A3-phosphorinan- 4,6-dione (2), 2-methoxy-1,3,5-trimethyl-1,3,5-triaza-2λ3-phosphorinan-4,6-dione (3) and 2-trimethylsiloxy-1,3,5-trimethyl-1,3,5-triaza-2λ3-phosphorinan-4,6-dione (5) with hexafluoracetone are described. In the case of 2 and 3 the reaction furnished the spirocyclic compounds 7 and 8. 2-Bis(2-chloroethyl)amino-1,3,5-triphenyl-1,3,5-triaza-2λ3-phosphorinan- 4,6-dione (4) did not react. In the case of 1 and 5 rearrangement reactions took place; the (2-chloroethyl)amino substituent of 1 reacted with one of two equivalents of hexafluoroacetone with formation of the spirocyclic phosphorane 6. The reaction of 5 with tetrabromoorthobenzoquinone gave the phosphoryl compound 9. Compounds 6 - 8 were characterized via their 1H-, 13C-, 19F- and 31P-NMR and mass spectra, compound 9 via its 1H-, 13C- and 31P-NMR and mass spectra. An X-ray crystal structure determination of 8 was conducted; in the six-membered ring the phosphorus atom lies 73 pm out of the plane of the other atoms, and displays trigonal bipyramidal coordination.

Keywords: 1,3,5-Trimethyl- and 1,5-dimethyl-3-phenyl-substituted 1,3,5-Triaza-7,10-dioxa-8,8,9,9-tetrakis( trifluoromethyl)-2λ5-phosphaspiro[4.5]decan; NMR Spectra; Mass Spectra; X-Ray

About the article

Received: 1994-12-16

Published Online: 2014-06-02

Published in Print: 1995-12-01


Citation Information: Zeitschrift für Naturforschung B, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-1995-1203.

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© 1946 – 2014: Verlag der Zeitschrift für Naturforschung. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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