A clue to elusive macrocycles: Unusually facile, spontaneous polymerization of a hexagonal diethynylbenzene macrocycle

Journal of Organic Chemistry

Volumn 71, Issue 1, 2006, Pages 401-404

  Nomoto, Akihiro ^a   Sonoda, Motohiro ^a   Yamaguchi, Yui ^a   Ichikawa, Tomoyuki ^a   Hirose, Keiji ^a   Tobe, Yoshito ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

MELTING; POLYMERIZATION; POLYMERS; SOLUBILITY;

DEHYDROOCTAMER; MELTING POINTS; SPONTANEOUS POLYMERIZATION;

BENZENE;

BENZENE DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; BROMINATION; CATALYSIS; CROSS COUPLING REACTION; CYCLIZATION; DEPROTECTION REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; POLYMERIZATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 31144457218     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051969e     Document Type: Article

References (31)

1. For recent reviews, see: (a) Grave, C.; Schlüter, A. D. Eur. J. Org. Chem. 2002, 3075-3098.
2. (b) Zhao, D.; Moore, J. S. Chem. Commun. 2003, 807-818.
3. (c) Höger, S. Chem.-Eur. J. 2004, 10, 1320-1329.
4. (d) Höger, S. In Acetylene Chemistry, Chemistry, Biology and Material Science, Diederich F., Stang, P. J., Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany, 2005; pp 427-452.
5. For recent reviews, see: (a) Haley, M. M.; Pak, J. J.; Brand, S. C. Top. Curr. Chem. 1999, 201, 81-130.
6. (b) Marsden, J. A.; Palmer, G. I.; Haley, M. M. Eur. J. Org. Chem. 2003, 2355-2369.
7. (c) Bunz, U. H. F. Top. Curr. Chem. 1999, 201, 131-161.
8. (d) Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Chem. Soc. Rev. 1999, 28, 107-119.
9. (e) Youngs, W. J.; Tessier, C. A.; Bradshaw, J. D. Chem. Rev. 1999, 99, 3153-3180.
10. For m-diethynylbenzene macrocycles, see: (a) Tobe, Y.; Utsumi, N.; Kawabata, K.; Naemura, K. Tetrahedron Lett. 1996, 37, 9325-9328.
11. (b) Tobe, Y.; Utsumi, N.; Nagano, A.; Sonoda, M.; Naemura, K. Tetrahedron 2001, 57, 8075-8083.
12. For dehydrobenzo[18]annulene, see: (a) Eglinton, G.; Galbraith, A. R. Proc. Chem. Soc., London 1957, 350-351.
13. (b) Behr, O. M.; Eglinton, G.; Raphael, A. R. Chem. Ind. 1959, 699-700.
14. (c) Eglinton, G.; Galbraith, A. R. J. Chem. Soc. 1960, 3614-3625.
15. (d) Zhou, Q.; Carroll, P. J.; Swager, T. M. J. Org. Chem. 1994, 59, 1294-1301.
16. (e) Wan, W. B.; Brand, S. C.; Pak, J. J.; Haley, M. M. Chem.-Eur. J. 2000, 6, 2044-2052.
17. (a) Tobe, Y.; Utsumi, N.; Nagano, A.; Naemura, K. Angew. Chem. Int. Ed. 1998, 37, 1285-1287.
18. (b) Tobe, Y.; Nagano, A.; Kawabata, K.; Sonoda, M.; Naemura, K. Org. Lett. 2000, 2, 3265-3268.
19. (c) Tobe, Y.; Utsumi, N.; Kawabata, K.; Nagano, A.; Adachi, K.; Araki, S.; Sonoda, M.; Hirose, K.; Naemura, K. J. Am. Chem. Soc. 2002, 124, 5350-5364.
20. For shape-persistent macrocycles having alkoxymethyl groups, see: (a) Lehmann, U.; Schluter, A. D. Eur. J. Org. Chem. 2000, 3483-3487.
21. (b) Henze, O.; Lentz, D.; Schlüter, A. D. Chem.-Eur. J. 2000, 6, 2362-2367.
22. (c) Henze, O.; Lentz, D.; Schäfer, A.; Franke, P.; Schlüter, A. D. Chem.-Eur. J. 2002, 8, 357-365.
23. (d) Grave, C.; Lentz, D.; Schäfer, A.; Samorì, P.; Rabe, J. P.; Franke, P.; Schlüter, A. D. J. Am. Chem. Soc. 2003, 125, 6907-6918.
24. Bartik, B.; Dembinski, R.; Bartik, T.; Arif, A. M.; Gladysz, J. A. New J. Chem. 1997, 21, 739-750.
25. Höger, S.; Bonrad, K.; Mourran, A.; Beginn, U.; Möller, M. J. Am. Chem. Soc. 2001, 123, 5651-5659.
26. In general, 1-arylbutadiynes with some exceptions are known to undergo spontaneous polymerization readily upon standing at ambient temperature. For example, see: (a) Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1991, 113, 9803-9810.
27. (b) Wan, W. B.; Haley, M. M. J. Org. Chem. 2001, 66, 3893-3901 and references therein.
28. -1 at 194.1 °C due to polymerization, giving dark brown solid.
29. Most of the known topochemical polymerizations of butadiyne derivatives are limited to dialkyl-substituted derivatives. See: (a) Wegner, G. Z. Naturforsch. B 1969, 24, 824-832.
30. (b) Enkelmann, V. Adv. Polym. Sci. 1984, 63, 91-136.
31. However, to our knowledge, one example of the light-induced polymerization of a diaryl-substituted butadiyne exists: (c) Baldwin, K. P.; Matzger, A. J.; Scheiman, D. A.; Tessier, C. A.; Vollhardt, K. P. C.; Youngs, W. J. Synlett 1995, 1215-1218.