Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The First Aziridinylguanidinates: New Precursors for Potentially Volatile Metal Guanidinates*

Peter Tutacz A , Ronny Syre A , Cristian G. Hrib A , Liane Hilfert A , Nancy Frenzel B , Edmund P. Burte B , Marcel Kühling A and Frank T. Edelmann A C
+ Author Affiliations
- Author Affiliations

A Chemisches Institut, Otto-von-Guericke-Universität Magdeburg, 39106 Magdeburg, Germany.

B Institut für Mikro- und Sensorsysteme, Otto-von-Guericke-Universität Magdeburg, 39106 Magdeburg, Germany.

C Corresponding author. Email: frank.edelmann@ovgu.de

Australian Journal of Chemistry 67(7) 1110-1114 https://doi.org/10.1071/CH14228
Submitted: 10 April 2014  Accepted: 28 April 2014   Published: 13 June 2014

Abstract

The first lithium-aziridinylamidinates, Li[(C2H4N)C(NR)2]·THF (R = iPr (3), Cy (4); iPr = isopropyl, Cy = cyclohexyl), have been prepared by addition of N-aziridinyllithium, C2H4NLi (2), to either N,N′-diisopropylcarbodiimide or N,N′-dicyclohexylcarbodiimide. The cyclohexyl derivative 4 was crystallised from both diethyl ether (Et2O) and THF to afford the crystalline solvent adducts {Li[(C2H4N)C(NR)2]·S}2 (4: S = THF; 4a: S = Et2O) which were structurally characterised by X-ray diffraction. In the solid state, these lithium-aziridinylamidinates comprise ladder-type dimeric molecular structures.


References

[1]  B. S. Lim, A. Rahtu, R. G. Gordon, Nat. Mater. 2003, 2, 749.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXosFWrt7w%3D&md5=7a3e9b1660fd7f5c2f373a6c291aa471CAS | 14578877PubMed |

[2]  B. S. Lim, A. Rahtu, J.-S. Park, R. G. Gordon, Inorg. Chem. 2003, 42, 7951.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXosVSnt7g%3D&md5=e2542b4d170f34877c4cfdc7746cb430CAS | 14632513PubMed |

[3]  J. Päiväsaari, C. L. Dezelah, D. Back, H. M. El-Kaderi, M. J. Heeg, M. Putkonen, L. Niinistö, C. H. Winter, J. Mater. Chem. 2005, 15, 4224.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) J. Barker, M. Kilner, Coord. Chem. Rev. 1994, 133, 219.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXlvFCjtbY%3D&md5=31b2a2b9544f74959a77b773b114adfdCAS |
      (b) F. T. Edelmann, Coord. Chem. Rev. 1994, 137, 403.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) F. T. Edelmann, Top. Curr. Chem. 1996, 179, 113.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) P. J. Bailey, S. Pace, Coord. Chem. Rev. 2001, 214, 91.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) H. Nagashima, H. Kondo, T. Hayashida, Y. Yamaguchi, M. Gondo, S. Masuda, K. Miyazaki, K. Matsubara, K. Kirchner, Coord. Chem. Rev. 2003, 245, 177.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) F. T. Edelmann, Adv. Organomet. Chem. 2008, 57, 183.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) F. T. Edelmann, Chem. Soc. Rev. 2009, 38, 2253.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) M. P. Coles, Chem. Commun. 2009, 3659,
         | Crossref | GoogleScholarGoogle Scholar |
      (i) A. A. Trifonov, Coord. Chem. Rev. 2010, 254, 1327.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) T. Li, J. Jenter, P. W. Roesky, Struct. Bond. 2010, 137, 165.
         | Crossref | GoogleScholarGoogle Scholar |
      (k) F. T. Edelmann, Chem. Soc. Rev. 2012, 41, 7657.
         | Crossref | GoogleScholarGoogle Scholar |
      (l) F. T. Edelmann, Adv. Organomet. Chem. 2013, 61, 55.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  C. F. H. Allen, F. W. Spangler, E. R. Webster, Org. Synth. 1950, 30, 38.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG3MXotVQ%3D&md5=668c0683697003cda68dfb497aa156b8CAS |

[6]  H. Gilman, N. N. Crouse, S. P. Massie, R. A. Benkeser, S. M. Spatz, J. Am. Chem. Soc. 1945, 67, 2106.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaH28Xmslak&md5=26bb012bcfb47f621425c64af06fe0e8CAS |

[7]  (a) A. F. Graefe, R. E. Meyer, J. Am. Chem. Soc. 1958, 80, 3939.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG1MXhslWqsA%3D%3D&md5=71cd30c622acd07dbbecb4ef55c6c360CAS |
      (b) G. Wittig, A. Hesse, Liebigs Ann. Chem. 1971, 746, 149.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) H. Bürger, U. Dämmgen, Z. Anorg. Allg. Chem. 1972, 394, 209.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) J. Harnisch, H. Legner, U. Szeimies-Seebach, G. Szeimies, Tetrahedon Lett. 1978, 3683.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) H. G. Zoch, E. Kinzel, G. Szeimies, Chem. Ber. 1981, 114, 968.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) U. Heywang, G. Szeimies, Chem. Ber. 1990, 123, 121.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  (a) J. R. Hagadorn, J. Arnold, Inorg. Chem. 1997, 36, 132.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XnsF2isb4%3D&md5=a8ea9fa2e15681faead5505b89739dd3CAS |
      (b) G. R. Giesbrecht, A. Shafir, J. Arnold, Dalton Trans. 1999, 3601,
         | Crossref | GoogleScholarGoogle Scholar |
      (c) C. L. Boyd, B. R. Tyrrell, P. Mountford, Acta Crystallogr. 2002, E58, m597.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) C. Villiers, P. Thuéry, M. Ephritikhine, Eur. J. Inorg. Chem. 2004, 4624,
         | Crossref | GoogleScholarGoogle Scholar |
      (e) P. C. Junk, M. L. Cole, Chem. Commun. 2007, 1579,
         | Crossref | GoogleScholarGoogle Scholar |
      (f) D. J. Brown, M. H. Chisholm, J. C. Gallucci, Dalton Trans. 2008, 1615,
         | Crossref | GoogleScholarGoogle Scholar |
      (g) S. Aharonovich, M. Kapon, M. Botoshansky, M. S. Eisen, Organometallics 2008, 27, 1869.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) H. Han, W. Li, H. Li, Acta Crystallogr. 2010, E66.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) S. Aharonovich, M. Botoshansky, Z. Rabinovich, R. M. Waymouth, M. S. Eisen, Inorg. Chem. 2010, 49, 1220.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) T. Chlupatý, Z. Padělková, A. Lyčka, A. Růžička, J. Organomet. Chem. 2011, 696, 2346.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  S. L. Aeilts, M. P. Coles, D. C. Swenson, R. F. Jordan, V. G. Young, Organometallics 1998, 17, 3265.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXksVKrsb8%3D&md5=224dd9ff04b3433d5e495d6689453b52CAS |

[10]  G. M. Sheldrick, SHELXL-97 Program for Crystal Structure Refinement 1997 (Universität Göttingen: Göttingen).

[11]  G. M. Sheldrick, SHELXS-97 Program for Crystal Structure Solution 1997 (Universität Göttingen: Göttingen).