High-yield macrocyclization via glaser coupling of temporary covalent templated bisacetylenes

Journal of Organic Chemistry

Volumn 62, Issue 14, 1997, Pages 4556-4557

  Höger, Sigurd ^a   Meckenstock, Anne Désirée ^a   Pellen, Heike ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE;

COVALENT BOND; CYCLIZATION; NOTE; STEREOSPECIFICITY; SYNTHESIS;

EID: 0030787454     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970350c     Document Type: Note

References (20)

1. Selected reviews and some new examples: (a) Tour, J. M. Chem. Rev. 1996, 96, 537. (b) Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1073.
2. Selected reviews and some new examples: (a) Tour, J. M. Chem. Rev. 1996, 96, 537. (b) Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1073.
3. (c) Timmermann, P.; Verboom, W.; van Veggel, F. C. J. M.; van Hoorn, W. P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1292. (d) Höger, S.; Enkelmann, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 2713.
4. (c) Timmermann, P.; Verboom, W.; van Veggel, F. C. J. M.; van Hoorn, W. P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 1292. (d) Höger, S.; Enkelmann, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 2713.
5. Host molecules based on phenylacetylene structures: (a) Morrison, D. L.; Höger, S. J. Chem. Soc., Chem. Commun. 1996, 2313. (b) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1989, 1714. (c) Mackeay, L. G.; Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 43. (d) Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596.
6. Host molecules based on phenylacetylene structures: (a) Morrison, D. L.; Höger, S. J. Chem. Soc., Chem. Commun. 1996, 2313. (b) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1989, 1714. (c) Mackeay, L. G.; Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 43. (d) Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596.
7. Host molecules based on phenylacetylene structures: (a) Morrison, D. L.; Höger, S. J. Chem. Soc., Chem. Commun. 1996, 2313. (b) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1989, 1714. (c) Mackeay, L. G.; Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 43. (d) Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596.
8. Host molecules based on phenylacetylene structures: (a) Morrison, D. L.; Höger, S. J. Chem. Soc., Chem. Commun. 1996, 2313. (b) Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1989, 1714. (c) Mackeay, L. G.; Anderson, H. L.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1992, 43. (d) Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596.
9. Staab, H. A.; Neunhoeffer, K. Synthesis 1974, 424.
10. Zhang, J.; Pesak, D. J.; Ludwig, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227.
11. (a) de Meijere, A.; Kozhushkov, S.; Haumann, T.; Boese, R.; Puls, C.; Cooney, M. J.; Scott, L. T. Chem. Eur. J. 1995, 1, 124.
12. (b) Boldi, A. M.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 486.
13. For recent articles dealing with template reactions see: (a) Anderson, S.; Anderson, H. L.; Sanders, J. K. M. Acc. Chem. Res. 1993, 26, 469. (b) Hoss, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 375. (c) Dietrich, B.; Viout, P.; Lehn, J.-M. Macrocyclic Chemistry; VCH: Weinheim, 1993; Chapter 3.3.
14. For recent articles dealing with template reactions see: (a) Anderson, S.; Anderson, H. L.; Sanders, J. K. M. Acc. Chem. Res. 1993, 26, 469. (b) Hoss, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 375. (c) Dietrich, B.; Viout, P.; Lehn, J.-M. Macrocyclic Chemistry; VCH: Weinheim, 1993; Chapter 3.3.
15. For recent articles dealing with template reactions see: (a) Anderson, S.; Anderson, H. L.; Sanders, J. K. M. Acc. Chem. Res. 1993, 26, 469. (b) Hoss, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 375. (c) Dietrich, B.; Viout, P.; Lehn, J.-M. Macrocyclic Chemistry; VCH: Weinheim, 1993; Chapter 3.3.
16. The GPC diagrams were measured in THF, and a UV detector operating at λ = 254 nm was used. The molecular weight was obtained from polystyrene calibration of the GPC columns.
17. To confirm that it is actually the cyclic trimer, we esterfied compotind 9 and compared the GPC diagram with the one obtained for the cyclization of 6.
18. 3 macrocyclic receptors by a templated triple macrolactamization (Hong, J.-I.; Namgoong, S. K.; Bernardi, A.; Still, W. C. J. Am. Chem. Soc. 1991, 113, 5111 ) and the formation of macrocyclic tetraesters by reaction on a porphyrin template (Mackey, L. G.; Bonar-Law, R. P.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1993, 1377) are also reported. However, in both cases the yields are relatively low, and the template was not removed after cyclization.
19. 3 macrocyclic receptors by a templated triple macrolactamization (Hong, J.-I.; Namgoong, S. K.; Bernardi, A.; Still, W. C. J. Am. Chem. Soc. 1991, 113, 5111 ) and the formation of macrocyclic tetraesters by reaction on a porphyrin template (Mackey, L. G.; Bonar-Law, R. P.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1993, 1377) are also reported. However, in both cases the yields are relatively low, and the template was not removed after cyclization.
20. 10 was prepared using our convergent strategy for the preparation of arylacetylene oligomers with ethynyl end groups (Höger, S.; Müller, S.; Karcher, L.; Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1997, 38(1), 72). A detailed experimental procedure for the preparation of 10 as well as the functionalization of the detemplated macrocycle will be published elsewhere.