Organic 'magic rings': The hydrogen bond-directed assembly of catenanes under thermodynamic control [2]

Journal of the American Chemical Society

Volumn 121, Issue 7, 1999, Pages 1599-1600

  Kidd, Timothy J ^a,b   Leigh, David A ^a,b   Wilson, Andrew J ^a,b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATENIN; MACROCYCLIC COMPOUND;

CATALYSIS; CHEMICAL REACTION KINETICS; CYCLIZATION; HYDROGEN BOND; LETTER; THERMODYNAMICS;

EID: 0033599365     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983106r     Document Type: Letter

References (33)

1. (a) Schill, G. Catenanes, Rotaxanes and Knots; Academic Press: New York, 1971.
2. (b) Dietrich-Buchecker, C.; Sauvage, J.-P. Bioorg. Chem. Frontiers 1991, 2, 195-247.
3. (c) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828.
4. (d) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311.
5. (e) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451-460.
6. (f) Hamilton, D. G.; Sanders, J. K. M.; Davies, J. E.; Clegg, W.; Teat, S. J. Chem. Commun. 1997, 897-898. DNA catenanes [Seeman, N. C. Annu. Rev. Biophys. Biomol. Struct. 1998, 27, 225-248] provide an exception to the kinetically controlled strategies.
7. (f) Hamilton, D. G.; Sanders, J. K. M.; Davies, J. E.; Clegg, W.; Teat, S. J. Chem. Commun. 1997, 897-898. DNA catenanes [Seeman, N. C. Annu. Rev. Biophys. Biomol. Struct. 1998, 27, 225-248] provide an exception to the kinetically controlled strategies.
8. Processes which utilize noncovalent forces to assemble an interlocked complex that is subsequently "captured" by irreversible covalent bond formation ("self-assembly with covalent modification") only operate under thermodynamic control before the final cyclization step [Amabilino, D. B.; Ashton, P. R.; Pérez-García, L.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 2378-2380]. "Strict self-assembly" pathways spontaneously and reversibly convert components into products at thermodynamic equilibrium [Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196].
9. Processes which utilize noncovalent forces to assemble an interlocked complex that is subsequently "captured" by irreversible covalent bond formation ("self-assembly with covalent modification") only operate under thermodynamic control before the final cyclization step [Amabilino, D. B.; Ashton, P. R.; Pérez-García, L.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1995, 34, 2378-2380]. "Strict self-assembly" pathways spontaneously and reversibly convert components into products at thermodynamic equilibrium [Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196].
10. (a) Gruter, G.-J. M.; de Kanter, F. J. J.; Markies, P. R.; Nomoto, T.; Akkerman, O. S.; Bickelhaupt, F. J. Am. Chem. Soc. 1993, 115, 12179-12180.
11. (b) Fujita, M.; Ibukuro, F.; Hagihara, H.; Ogura, K. Nature 1994, 367, 720-723.
12. (c) Fujita, M.; Ibukuro, F.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 4175-4176.
13. (d) Fujita, M.; Ibukuro, F.; Seki, H.; Kamo, O.; Imanari, M.; Ogura, K. J. Am. Chem. Soc. 1996, 118, 899-900.
14. (e) Fujita, M.; Aoyagi, M.; Ibukuro, F.; Ogura, K.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 611-612.
15. (f) Whang, D.; Park, K.-M.; Heo, J.; Ashton, P.; Kim, K. J. Am. Chem. Soc. 1998, 120, 4899-4900.
16. (g) Try, A. C.; Harding, M. M.; Hamilton, D. G.; Sanders, J. K. M. Chem. Commun. 1998, 723-724.
17. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
18. (b) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
19. (c) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
20. (d) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
21. For tandem RORCM reactions which covert one ring system into a different ring system see: Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634-6640.
22. 13,14 For the synthesis of a molecular knot by RCM see: Dietrich-Buchecker, C.; Rapenne, G.; Sauvage, J.-P. Chem. Commun. 1997, 2053-2054.
23. 13,14 For the synthesis of a molecular knot by RCM see: Dietrich-Buchecker, C.; Rapenne, G.; Sauvage, J.-P. Chem. Commun. 1997, 2053-2054.
24. For evidence of some catenane formation during RORCM of macrocycles without recognition sites see: Wolovsky, R. J. Am. Chem. Soc. 1970, 92, 2132-2133; Wasserman, E.; Ben-Efraim, D. A.; Wolovsky, R. J. Am. Chem. Soc. 1970, 92, 2133-2135. For a recent discussion of the mechanism involved in those reactions see: Gruter, G.-J. M.; Akkerman, O. S.; Bickelhaupt, F. Tetrahedron 1996, 52, 2565-2572.
25. For evidence of some catenane formation during RORCM of macrocycles without recognition sites see: Wolovsky, R. J. Am. Chem. Soc. 1970, 92, 2132-2133; Wasserman, E.; Ben-Efraim, D. A.; Wolovsky, R. J. Am. Chem. Soc. 1970, 92, 2133-2135. For a recent discussion of the mechanism involved in those reactions see: Gruter, G.-J. M.; Akkerman, O. S.; Bickelhaupt, F. Tetrahedron 1996, 52, 2565-2572.
26. For evidence of some catenane formation during RORCM of macrocycles without recognition sites see: Wolovsky, R. J. Am. Chem. Soc. 1970, 92, 2132-2133; Wasserman, E.; Ben-Efraim, D. A.; Wolovsky, R. J. Am. Chem. Soc. 1970, 92, 2133-2135. For a recent discussion of the mechanism involved in those reactions see: Gruter, G.-J. M.; Akkerman, O. S.; Bickelhaupt, F. Tetrahedron 1996, 52, 2565-2572.
27. The metathesis "catalyst" is actually a precatalyst or reaction initiator, so a small amount of macrocycle/catenane is lost through cross metathesis with the benzylidene ligand of 5.
28. 2Cl/iPrOH) allowed the separation of individual catenane diolefin isomers EE-4 and EZ-3.
29. 2 can be problematical and therefore the RORCM reactions require rigorous degassing before and during the experiment.
30. Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310.
31. 13C NMR chemical shifts of allylic carbons and characteristic IR bands [Williams, D. H.; Fleming, I. Spectroscopic Methods in Organic Chemistry, 4th ed., revised; McGraw-Hill: London, 1989].
32. Note Added in Proof. For a recent example involving the temporary blocking of a cyclophane cavity in another catenane synthesis employing RCM see: Hamilton, D. G.; Sanders, J. K. M. Chem. Commun. 1998, 1749-1750.
33. Note Added in Proof. A π-electron rich/π-electron poor heterocircuit catenane synthesis by RORCM has recently been reported [Hamilton, D. G.; Feeder, N.; Teat, S. J.; Sanders, J. K. M. New J. Chem. 1998, 1019-1021], although solubility-limited concentrations and slow reaction kinetics [see footnote 10] make the system only quasi-reversible thus far and consequently the product distribution is not under strict thermodynamic control.