Skip to main content
SpringerLink
Log in

X-ray structure and conformation of some (R,R)-N,N′-tetrasubsubstituted 1,2-diamines

  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

The conformational arrangement of a series of (R,R)-N,N′-tetrasubstituted cyclohexyl-1,2-diamines have been examined by X-ray crystallography.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1.
Scheme 2.
Scheme 3.
Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Scheme 4.
Fig. 5.
Fig. 6.
Fig. 7.
Fig. 8.
Fig. 9.
Fig. 10.

Similar content being viewed by others

References

  1. (a) Costa, A.M.; Jimeno, C.; Gavenonis, J.; Carroll, P.J.; Walsh, P.J. J. Am. Chem. Soc. 2002, 124, 6929; (b) Annunziata, R.; Benaglia, M.; Caporale, M.; Raimondi, L. Tetrahedron: Asymmetr. 2002, 13, 2727; (c) Vasse, J.-L.; Stranne, R.; Zalubovskis, R.; Gayet, C.; Moberg, C. J. Org. Chem 2003, 68, 3258; (d) Johansson, M.J.; Schwartz, L.; Amedjkouh, M.; Kann, N. Tetrahedron: Asymm. 2004, 15, 3531.

  2. (a) Kizirian, J.-C.; Caille, J.-C.; Alexakis, A. Tetrahedron Lett. 2003, 44, 8893; (b) Cobb, A.J.A.; Marson, C.M. Tetrahedron: Asymmetr. 2001, 12, 1547.

  3. (a) Bennani, Y.L.; Hanessian, S. Chem. Rev. 1997, 97, 3161; (b) Lucet, D.; Gall, T.L.; Mioskowski, C. Angew. Chem. 1998, 110, 2724; (c) Fache, F.; Schulz, E.; Tommassino, M.; Lemaire, M. Chem. Rev. 2000, 100, 2159.

  4. (a) Kim, G.-J.; Kim, S.-H.; Chong, P.-H.; Kwon, M.-A. Tetrahedron Lett. 2002, 43, 8059; (b) Hanessian, S.; Derlorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754; (c) Alexakis, A.; Chauvin, A.-S.; Stouvenel, R.; Vrancken, E.; Mutti, S.; Mangeney, P. Tetrahedron: Asymmetr. 2001, 12, 1171.

  5. Remenar, J.F.; Lucht, B.L.; Collum, D.B. J. Am. Chem. Soc. 1997, 119, 5567; for an additional example see reference 2(a).

    Article  CAS  Google Scholar 

  6. Review: (a) Lucet, D.; Gall, T. Le; Mioskowski, C. Angew Chem. Int. Ed. Engl. 1998, 37, 2580; For some examples see (a) Corey, E.J.; Sarshar, S.; Azimioara, M.D.; Newbold, R.C.; Noe, M.C. J. Am. Chem. Soc. 1996, 118, 7851; (b) Kobayahi, S.; Horibe, M. J. Am. Chem. Soc. 1994, 116, 9805.

  7. (a) Murray-Rust, P.; Riddell, F.G. Can. J. Chem. 1975, 53, 1933; (b) Zhao, S.; Freeman, J.P.; Chidester, C.G.; VonVolgtander, P.F.; Mizsak, S.A.; Szmuszkovicz, J. J. Org. Chem. 1993, 58, 4043.

  8. (a) Corey, E.J.; Sarshar, S.; Azimioara, M.D.; Newbold, R.C.; Noe, M.C. J. Am. Chem. Soc. 1996, 118, 7851; (b) Cole, A.P.; Root, D.E.; Mukherjee, P.; Solomon, E.I.; Stack, T.D.P. Science 1996, 273, 1848.

  9. Perlasamy, M.; Sivakumar, S.; Reddy, M.N.; Padmaja, M. Org. Lett. 2004, 6, 265.

    Google Scholar 

  10. Shkol’nikova, L.M.; Polyanchuk, G.V.; Dyatlova, N.M.; Poral-Koshits, M.A.; Yashunskii, V.G. Zh. Strukt. Khim. (Russ.) (J. Struct. Chem.) 1983, 24, 92; (b) Sun, Y.; Martell, A.R.; Reibensples, J.H.; Reichert, D.E.; Walsh, M.J. Inorg. Chem. 2000, 39, 1480. For other non-related 1,2-diamino cyclohexane derived 1,2-diamines, see reference 23.

  11. Coumbarides, G.S.; Boyd, E.; Eames, J.; Jones, R.V.H.; Stenson, R.; Suggate, M.J. Tetrahedron Lett. 2005, 46, 1921.

    Article  Google Scholar 

  12. For related derivatives see (a) Gawronski, J.; Kazmierczak, F.; Gawronska, K.; Rychlewska, U.; Norden, B.; Holmen, A. J. Am. Chem. Soc. 1998, 120, 12083; (b) Doi, M.; Ishida, T.; Inoue, M. Chem. Pharm. Bull. 1990, 38, 1815.

  13. North, A.C.T.; Phillips, D.C.; Mathews, F.S. Acta Crystallogr. Sect. A 1968, 24, 451.

    Article  Google Scholar 

  14. Harms, K.; Wocadlo, S. XCAD4-CAD4, Data Reduction; University of Marburg, Marburg, Germany, 1995.

  15. Hooft, R.; Nonius, B.V. COLLECT, Data Collection Software, data collection and processing user interface, 1998.

  16. (a) Otwinowski, Z.; Minor, W. In Methods in Enzymology, Macromolecular Crystallography, Part A, Vol. 276; 1Carter Jr, C.W.; Sweet, R.M. Eds.; Academic Press, 1997; pp. 307. (b) Otwinowski, Z.; Minor, W. DENZO, Data Collection and Processing Software, 1999.

  17. Mackay, S.; Gilmore, C.J.; Edwards, C.; Tremayne, M.; Stewart, N.; Shankland, K.; Maxus, A Computer Program for the Solution and Refinement of Crystal Structures from Diffraction Data.

  18. Sheldrick, G.M.; SADABS, Bruker Nonius Area Detector Scaling and Absorption Correction, 2003 (V2.10).

  19. SHELX97 [Includes SHELXS97, SHELXL97, CIFTAB (and SHELXA)], Programs for Crystal Structure Analysis (Release 97-2). Institüt für Anorganische Chemie der Universität, Tammanstrasse 4, D-3400 Göttingen, Germany, 1998.

  20. Farrugia, L.J. ORTEP3 for Windows, J. Appl. Crystallogr. 1997, 30, 565.

    Google Scholar 

  21. Spek, A.L.; PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 1998.

    Google Scholar 

  22. Farrugia, L.J. WINGX, J. Appl. Cryst. 1999, 32, 837.

    Article  Google Scholar 

  23. (a) Tinant, B.; Parfonry, A.; Germain, G.; Declercq, J.P.; van. Meerssche, M. Bull. Soc. Chim. Belg., 1983, 92, 405; (b) Parfonry, A.; Tinant, B.; Declercq, J.P.; Meerssche, M. van. Bull. Soc. Chim. Belg. 1983, 92, 437; (c) Parfonry, A.; Declercq, J.P.; Tinant, B.; Meerssche, M. van.; Schweiss, P. Acta Crystallogr., Sect. B: Struct. Sci. 1988, 44, 435; (d) Hu, K.; Krakowiak, K.E.; Bradshaw, J.S.; Dalley, N.K.; Xue, G.; Izatt, R.M. J. Heterocycl. Chem., 1999, 36, 347; (e) Schneider, G.; Schollmeyer, D.; Pindur, U. Pharmazie, 1998, 53, 361; (f) Yeh, M.C.P.; Chuang, C.N.; Yiu, C.H. Tetrahedron Lett., 1997, 38, 7387; (g) Sun, Y.; Martell, A.R.; Reibenspies, J.H.; Reichert, D.E.; Welch, M.J. Inorg. Chem., 2000, 39, 1480; (h) Peters, K.; Peters, E.M.; Schnering, H.G. von; Schulze, R.; Beckhaus, H.D.; Ruchardt, C. Z. Kristallogr., 1997, 212, 76; (i) Welle, F.; Verevkin, S.P.; Keller, M.; Beckhaus, H.D.; Ruchardt, C. Chem. Ber., 1994, 127, 697.

Download references

Acknowledgments

We are grateful to The Royal Society, The University of London Central Research Fund and Syngenta (Grangemouth, Scotland) for their financial support. We thank EPSRC National Crystallography Service (Southampton University) for data collection.

Author information

Authors and Affiliations

  1. Syngenta, Grangemouth Manufacturing Centre, Earls Road, Grangemouth, FX3 8XG, Scotland

    Ewan Boyd & Ray. V. H. Jones

  2. Department of Chemistry, Queen Mary, University of London, Mile End Road, London, E1 4NS, UK

    Gregory S. Coumbarides, Jason Eames, Majid Motevalli & Michael J. Suggate

  3. Syngenta, Global Specialist Technology, PO Box A38, Leeds Road, Huddersfield, HD2 1FF, UK

    Rachel A. Stenson

  4. Department of Chemistry, University of Hull, Cottingham Road, Kingston upon Hull, HU6 7RX, UK

    Jason Eames

Authors
  1. Ewan Boyd
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gregory S. Coumbarides
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jason Eames
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ray. V. H. Jones
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Majid Motevalli
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Rachel A. Stenson
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Michael J. Suggate
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jason Eames.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Boyd, E., Coumbarides, G.S., Eames, J. et al. X-ray structure and conformation of some (R,R)-N,N′-tetrasubsubstituted 1,2-diamines. J Chem Crystallogr 36, 263–269 (2006). https://doi.org/10.1007/s10870-005-9018-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-005-9018-8

KEY WORDS:

Search

Navigation