Macrocyclic cyclophane belts via double Diels-Alder cycloadditions: Macroannulation of bisdienes by bisdienophiles. Synthesis of a key precursor to an [8]cyclacene

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 1983-1986

  Cory, Robert M ^a   McPhail, Cameron L ^a   Dikmans, Antonius J ^a   Vittal, Jagadese J ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; PHENANTHRENE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030010393     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00263-8     Document Type: Article

References (10)

1. Belt-Shaped Cyclophanes. 1. For the next paper in this series see the following paper in this issue.
2. Cory, R. M.; McPhail, C. L.; Dikmans, A. J. Tetrahedron Lett. 1993, 34, 7533-7536.
3. Approaches to other cyclacenes: Girreser, U.; Giuffrida, D.; Kohnke, F. H.; Mathias, J. P.; Philp, D.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 119-125; Kohnke, F. H.; Mathias, J. P.; Stoddart, J. F. Top. Curr. Chem. 1993, 165, 1-67.
4. Approaches to other cyclacenes: Girreser, U.; Giuffrida, D.; Kohnke, F. H.; Mathias, J. P.; Philp, D.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 119-125; Kohnke, F. H.; Mathias, J. P.; Stoddart, J. F. Top. Curr. Chem. 1993, 165, 1-67.
5. Approaches to cyclacenes and beltenes which have not yet reached the macrocycle stage: Alder, R. W.; Allen, P. R.; Edwards, L. S.; Fray, G. I.; Fuller, K. E.; Gore, P. M.; Hext, N. M.; Perry, M. H.; Thomas, A. R.; Turner, K. S. J. Chem. Soc., Perkin Trans. 1 1994, 3071-3077; Graham, R. J.; Paquette, L. A. J. Org. Chem. 1995, 60, 5770-5777.
6. Approaches to cyclacenes and beltenes which have not yet reached the macrocycle stage: Alder, R. W.; Allen, P. R.; Edwards, L. S.; Fray, G. I.; Fuller, K. E.; Gore, P. M.; Hext, N. M.; Perry, M. H.; Thomas, A. R.; Turner, K. S. J. Chem. Soc., Perkin Trans. 1 1994, 3071-3077; Graham, R. J.; Paquette, L. A. J. Org. Chem. 1995, 60, 5770-5777.
7. Review: Schröder, A.; Mekelburger, H.-B.; Vögtle, F. Top. Curr. Chem. 1994, 172, 179-201.
8. Closely related studies involved macrocycle formation by double Diels-Alder dimerization of a diene-quinone: Godt, A.; Enkelmann, V.; Schlüter, A. D. Angew. Chem. Int. Ed. Engl. 1989, 28, 1680-1682.
9. -1, F(000) = 1760, and T = 296 K. The final refinements, performed using the SHELXL-93 programs (G.M. Sheldrick, University of Göttingen, Germany), based on all 14520 independent reflections and 839 variables, led to R1 = 0.1472, wR2 = 0.3623. The asymmetric unit contains two independent molecules, in which all eight of the hexyl groups (four in each molecule) are disordered, with the exception of the first carbon atom in each of the hexyl chains. This disorder limits the overall precision of the structure (in terms of agreement factors), but the structure of the macrocyclic core has been determined with good precision for each of the independent molecules.
10. Chiba, T.; Kenny, P. W.; Miller, L. L. J. Org. Chem. 1987, 52, 4327-4331.