Novel Crown Ether Assemblies: The Role of Isobenzofurans for Attaching Crown Ethers to Rigid Molecular Racks in a Geometrically Precise Fashion

Synlett

Volumn 1997, Issue 1, 1997, Pages 47-50

  Warrener, Ronald N ^a   Wang, Shudong ^a   Russell, Richard A ^b   Gunter, Maxwell J ^c  

^a CENTRAL QUEENSLAND UNIVERSITY   (Australia)

^b DEAKIN UNIVERSITY   (Australia)

^c UNIVERSITY OF NEW ENGLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002025740     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-701     Document Type: Article

References (20)

1. "Crown Compounds: Towards Future Applications", Ed S. R. Cooper, VCH, NY, 1992.
2. inter alia Lawson, J. M.; Craig, D. C.; Oliver, A. M.; Paddon-Row, M. N. Tetrahedron 1995, 51, 3841 and references therein. Kumar, K.; Tepper, R. J.; Zeng, Y.; Zimmt, M. B. J. Org. Chem. 1995, 60, 4051 and references therein.
3. inter alia Lawson, J. M.; Craig, D. C.; Oliver, A. M.; Paddon-Row, M. N. Tetrahedron 1995, 51, 3841 and references therein. Kumar, K.; Tepper, R. J.; Zeng, Y.; Zimmt, M. B. J. Org. Chem. 1995, 60, 4051 and references therein.
4. Klarner, F.-G.; Benkhoff, J.; Boese, R.; Burkert, U.; Kamieth, M.; Naatz, U. Angew. Chem. Int. Ed. Engl. 1996, 35, 1130. Benkhoff, J.; Boese, R.; Klarner, F.-G; Wigger, A. E. Tetrahedron Lett. 1994, 35, 73.
5. Klarner, F.-G.; Benkhoff, J.; Boese, R.; Burkert, U.; Kamieth, M.; Naatz, U. Angew. Chem. Int. Ed. Engl. 1996, 35, 1130. Benkhoff, J.; Boese, R.; Klarner, F.-G; Wigger, A. E. Tetrahedron Lett. 1994, 35, 73.
6. 5
7. Warrener, R. N.; Elsey, G. M.; Sankar, I. V.; Butler, D. N.; Pekos, P.; Kennard, C. H. L. Tetrahedron Lett., 1994, 35, 6745.
8. Warrener, R. N.; Houghton, M. A.; Schultz, A. C.; Keene, F. R.; Kelso, L. S.; Dash, R.; Butler, D. N. Chem. Commun. 1996, 1151. Warrener, R. N.; Ferreira, A. B. B.; Schultz, A. C.; Butler, D. N.; Keene, F. R.; Kelso, L. S. Angew. Chem. 1996, 108, 2651. Warrener, R. N.; Schultz, A. C.; Houghton, M. A.; Butler, D. N. Tetrahedron, 1997, in press.
9. Warrener, R. N.; Houghton, M. A.; Schultz, A. C.; Keene, F. R.; Kelso, L. S.; Dash, R.; Butler, D. N. Chem. Commun. 1996, 1151. Warrener, R. N.; Ferreira, A. B. B.; Schultz, A. C.; Butler, D. N.; Keene, F. R.; Kelso, L. S. Angew. Chem. 1996, 108, 2651. Warrener, R. N.; Schultz, A. C.; Houghton, M. A.; Butler, D. N. Tetrahedron, 1997, in press.
10. Warrener, R. N.; Houghton, M. A.; Schultz, A. C.; Keene, F. R.; Kelso, L. S.; Dash, R.; Butler, D. N. Chem. Commun. 1996, 1151. Warrener, R. N.; Ferreira, A. B. B.; Schultz, A. C.; Butler, D. N.; Keene, F. R.; Kelso, L. S. Angew. Chem. 1996, 108, 2651. Warrener, R. N.; Schultz, A. C.; Houghton, M. A.; Butler, D. N. Tetrahedron, 1997, in press.
11. Sielcken, O. E.; van Tilborg, M. M.; Roks, M. F. M.; Hendriks, R.; Drenth, W.; Nolte, R. J. M. J. Am. Chem. Soc. 1987, 109, 4261.
12. Geldard, J. F.; Lions, F. J. Org. Chem. 1965, 30, 318.
13. Where isobenzofurans are being reacted with ring-strained substrates, eg 15, which themselves react with s-tetrazines, then it is necessary to use the isolated dihydropyridazine 10 as the isobenzofuran source; where substrates, eg 25, are not reactive towards s-tetrazines, in situ generation of isobenzofuran can be used in a one-pot reaction containing epoxynaphthalene, s-tetrazine and the substrate to undergo cycloaddition. Warrener, R. N. J. Am. Chem. Soc. 1971, 95, 2346. Russell, R. A.; Longmore, R. W.; Warrener, R. N. J. Chem. Ed. 1992, 69, 16410.
14. Where isobenzofurans are being reacted with ring-strained substrates, eg 15, which themselves react with s-tetrazines, then it is necessary to use the isolated dihydropyridazine 10 as the isobenzofuran source; where substrates, eg 25, are not reactive towards s-tetrazines, in situ generation of isobenzofuran can be used in a one-pot reaction containing epoxynaphthalene, s-tetrazine and the substrate to undergo cycloaddition. Warrener, R. N. J. Am. Chem. Soc. 1971, 95, 2346. Russell, R. A.; Longmore, R. W.; Warrener, R. N. J. Chem. Ed. 1992, 69, 16410.
15. Prepared by dehydrogenation (DDQ, 51%, m.p. 169-170°C) of the [4π+2π]adduct of 2,3-dimethoxy-1,3-butadiene and 1,4-di(4-tert-butylphenyl)-but-2-en-1,4-dione (75%, m.p. 176-177°C).
16. Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7071.
17. Precedent for such dehydrations have been found in other U-shaped cavity systems, Warrener, R. N.; Fairlie, D. P.; Russell, R. A., unpublished results.
18. Warrener, R. N.; Wang, S.; Butler, D. N.; Russell, R. A. Synlett. 1997, 44.
19. We have recently discovered a new coupling process for stereospecifically assembling polyalicyclic nanostructures from the reaction of smaller functionalised carbocyclic dienophiles with fused epoxycyclobutanes and these crown compounds are admirably suited building blocks for this procedure.
20. 3) δ 46.55, 51.37, 58.75, 69.23, 69.31, 69.43, 70.33, 70.45, 70.76, 79.44, 85.49, 107.00, 107.92, 135.64, 137.21, 148.18, 148.37, 168.89.