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DOI: 10.1039/A700010C (Paper) Reference Section for: Chem. Commun., 1997, 1023-1024

A new building block technique based on cycloaddition chemistry for the regiospecific linking of alicyclic sub-units as a route to large, custom-functionalised structures

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Ronald N. Warrener, Austin C. Schultz, Douglas N. Butler, Shudong Wang, Indu B. Mahadevan and Richard A. Russell

Abstract

A new building BLOCK approach to synthesis has been developed where functionalised norbornenes (BLOCK A) are coupled with functionalised cyclobutene epoxides (BLOCK B) to produce A + B structures of defined geometry; use of a dual (spacer) BLOCK allows the formation of large structures where crown ether, ligand and redox centres are incorporated in similar or mixed pairings.

References

  1. J. M. Lehn, Supramolecular Chemistry—Concepts and Perspectives, VCH, Weinheim, 1995 Search PubMed.
  2. R. N. Warrener, M. A. Houghton, A. C. Schultz, F. R. Keene, L. S. Kelso, R. Dash and D. N. Butler, Chem. Commun., 1996, 1151 RSC; R. N. Warrener, A. B. B. Ferreira, A. C. Schultz, D. N. Butler, F. R. Keene and L. S. Kelso, Angew. Chem., Int. Ed. Engl., 1996, 108, 2651.
  3. R. N. Warrener, S. Wang, R. A. Russell and M. J. Gunter, Synlett, 1997, 47.
  4. R. Huisgen, Angew. Chem., Int. Ed. Engl., 1977, 16, 572 CrossRef.
  5. E. F. Ulmann and W. A. Henderson, J. Am. Chem. Soc., 1966, 88, 4942 CrossRef.
  6. V. G. Seitz and H. Wassmuth, Chem. -Z., 1988, 112, 80 Search PubMed; F. Thalhammer, U. Wallfahrer and J. Sauer, Tetrahedron Lett., 1988, 29, 3231 CrossRef CAS; G. Seitz and C. H. Gerninghaus, Pharmazie, 1994, 49, 102 Search PubMed.
  7. T. Mitsudo, H. Naruse, T. Kondo, Y. Ozaki and Y. Watanabe, Angew. Chem., Int. Ed. Engl., 1994, 33, 580 CrossRef; T. Mitsudo, K. Kokuryo, T. Shinsugi, Y. Nakagawa, Y. Watanabe and Y. Takegami, J. Org. Chem., 1979, 44, 4492 CrossRef CAS.
  8. L. A. Paquette, F. Bellamy, M. C. Bohm and R. J. Gleiter, J. Org. Chem., 1980, 45, 4913 CrossRef CAS.
  9. J. M. Lawson, A. M. Oliver, D. F. Rothenfluh, Y.-Z. An, G. A. Ellis, M. G. Ranasinghe, S. A. Khan, A. G. Franz, P. S. Ganapathi, M. J. Shephard, M. N. Paddon-Row and Y. Rubin, J. Org. Chem., 1996, 61, 5032 CrossRef CAS.
  10. R. N. Warrener, D. Margetic, E. R. T. Tiekink and R. A. Russell, Synlett, 1997, 196 CAS.
  11. R. N. Warrener, D. Margetic, A. C. Schultz and R. A. Russell, unpublished results.
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