Double [2+2] photocycloaddition: Topochemical conversion of 4-methyl-7-styrylcoumarin dimorphs into a strained cyclophane

Crystal Growth and Design

Volumn 7, Issue 4, 2007, Pages 713-718

  Moorthy, Jarugu Narasimha ^a   Venkatakrishnan, Parthasarathy ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34247501826     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg060652k     Document Type: Article

References (67)

1. (a) Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433.
2. (b) Venkatesan, K.; Ramamurthy, V. In Photochemistry in Organized and Constrained Media, Ramamurthy, V., Ed.; VCH: New York, 1991, p 133.
3. (c) Keating, A. E; Garcia-Garibay, M. A. In Molecular and Supramolecular Photochemistry; Ramamurthy, V., Schanze, K. S., Eds.; Marcel Dekker: New York. 1998; Vol. 2, Chapter 5.
4. (d) Toda, F. Acc. Chem. Res. 1995, 28, 480.
5. (e) Toda, F.; Tanaka, K. Chem. Rev. 2000, 100, 1025.
6. (f) Toda, F. Top. Curr. Chem. 2005, 254, 1.
7. (a) Cohen, M. D.; Schmidt, G. M. J. J. Chem. Soc. 1964, 1996.
8. (b) Cohen, M. D.; Schmidt, G. M. J.; Sonntag, F. I. J. Chem. Soc. 1964, 2000.
9. (c) Schmidt, G. M. J. J. Chem. Soc. 1964, 2014.
10. (d) Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647.
11. (e) Cohen, M. D. Angew. Chem., Int. Ed. Engl. 1975, 14, 386.
12. Bregman, J.; Osaki, K.; Schmidt, G. M. J.; Sonntag, F. I. J. Chem. Soc. 1964, 2021.
13. For photodimerizations using various strategies, see (a) Moorthy, J. N.; Venkatesan, K. J. Org. Chem. 1991, 56, 6957.
14. (b) Moorthy, J. N.; Weiss, R. G.; Venkatesan, K. J. Org. Chem. 1992, 57, 3292.
15. (c) Rao, K. S. S. P.; Hubig, S. M.; Moorthy, J. N.; Kochi, J. K. J. Org. Chem. 1999, 64, 8098 and references therein.
16. (d) Herrmann, W. Wehrle, S.; Wenz, Z. Chem. Commun. 1997, 1709.
17. (e) Coates, G. W.; Dunn, A. R.; Henling, L. M.; Ziller, J. W.; Lobkovsky, E. B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 3641.
18. (f) Jon, S. Y.; Ko, Y. H.; Park, S. H.; Kim, H. J.; Kim, K. Chem. Commun. 2001, 1938.
19. (g) Ohba, S.; Hosomi, H.; Ito, Y. J. Am. Chem. Soc. 2001, 123, 6349.
20. (h) Varshney, D. B.; Papaefstathiou, G. S.; MacGillivray, L. R. Chem. Commun. 2002, 1964.
21. (i) Hamilton, T. D.; Papaefstathiou, G. S.; MacGillivray, L. R. J. Am. Chem. Soc. 2002, 124, 11606.
22. (j) Hoang, T.; Lauher, J. W.; Fowler, F. W. J. Am. Chem. Soc. 2002, 124, 10656.
23. (k) Friščič, T.; MacGillivray, L. R. Chem. Commun. 2003, 1306.
24. (l) Gao, X.; Friščič, T.; MacGillivray, L. R. Angew. Chem., Int. Ed. 2003, 42, 232.
25. (m) Friščič, T.; Drab, D. M.; MacGillivray, L. R. Org. Lett. 2004, 6, 4647.
26. (n) Papaefsthathiou, G. S.; Zhong, Z.; Geng, L.; MacGillivray, L. R. J. Am. Chem. Soc. 2004, 126, 9158.
27. (o) Toh, N. L.; Nagarathinam, M.; Vittal, J. J. Angew. Chem., Int. Ed. 2005, 44, 2237.
28. (p) Natarajan, A.; Mague, J. T.; Venkatesan, K.; Ramamurthy, V. Org. Lett. 2005, 7, 1895.
29. For polymerization with diolefins, see (a) Hasegawa, M. Adv. Polym. Sxi. 1982, 42, 1.
30. (b) Hasegawa, M. Chem. Rev. 1983, 83, 507.
31. (c) Dilling, W. L. Chem. Rev. 1983, 83, 1. For polymerization of diand triacetylenes, see
32. (d) Kane, J. J.; Liao, R.-F.; Lauher, J. W.; Fowler, F. M. J. Am. Chem. Soc. 1995, 117, 12003.
33. (e) Xiao, J.; Yang, M.; Lauher, J. W.; Fowler, F. W. Angew. Chem. Int. Ed. 2000, 39, 2132.
34. (f) Hoang, T.; Lauher, J. W.; Fowler, F. M. J. Am. Chem. Soc. 2002, 124, 10656.
35. (g) Ouyang, X.; Fowler, F. M.; Lauher, J. W. J. Am. Chem. Soc. 2003, 125, 12400.
36. (h) Sun, A.; Lauher, J. W.; Goroff, N. S. Science 2006, 312, 1030.
37. For double dimerizations, see (a) Green, B. S.; Schmidt, G. M. J. Tetrahedron Lett. 1970, 49, 4249.
38. (b) Hasegawa, M.; Saigo, K.; Mori, T.; Uno, H.; Nohara, M.; Nakanishi, H. J. Am. Chem. Soc. 1985, 107, 2788.
39. (c) Hasegawa, M.; Endo, Y.; Aoyama, M.; Saigo, K. Bull. Chem. Soc. Jpn. 1989, 62, 1556.
40. (d) Venugopalan, P.; Venkatesan, K. Bull. Chem. Soc. Jpn. 1990, 63, 2368.
41. (a) Waldeck, D. H. Chem. Rev. 1991, 91, 415.
42. (b) Arai, T.; Tokumaru, K. Chem. Rev. 1993, 93, 23.
43. (X) (a) Muszkat, K. A. Top. Curr. Chem. 1980, 88, 89.
44. (b) Laarhoven, W. H. In Photochromism, Molecules and Systems; Durr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990; p 270.
45. Moorthy, J. N.; Venkatakrishnan, P.; Savitha, G.; Weiss, R. G. Photochem. Photobiol Sci. 2006, 5, 903.
46. Gnanaguru, K.; Ramasubbu, N.; Venkatesan, K.; Ramamurthy, V. J. Org. Chem. 1985, 50, 2337.
47. (a) Bernstein, J. Polymorphism in Molecular Crystals: Clarendon: Oxford, 2002.
48. (b) For a special issue on Polymorphism in Crystals: Fundamentals, Prediction and Industrial Practice, see Cryst. Growth Des. 2003, 3(6).
49. (c) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629.
50. (d) Bernstein, J. Organic Solid State Chemistry; Desiraju, G. R., Ed., Elsevier: Amsterdam, 1987, p 471.
51. (e) Braga, D.; Grepioni, F. Chem. Soc. Rev. 2000, 29, 229.
52. For polymorphism of drugs, dyes, and explosives, see for example: (a) Vrcelj, R. M.; Sherwood, J. N.; Kennedy, A. R.; Gallagher, H. G.; Gelbrich, T. Cryst. Growth Des. 2003, 3, 1027.
53. (b) Sheth, A. R.; Bates, S.; Muller, F. X.; Grant, D. J. W. Cryst. Growth Des. 2004, 4, 1091.
54. (c) Thallapally, P. K.; Jetti, R. K. R.; Katz, A. K.; Carrell, H. L.; Singh, K.; Lahiri, K.; Kotha, S.; Boese, R.; Desiraju, G. R. Angew. Chem., Int. Ed. 2004, 43, 1149.
55. (d) Roy, S.; Aitipamula, S.; Nangia, A. Cryst. Growth Des. 2005, 5, 2268.
56. 4-Styrylcoumarins that are very different from the present diolefinic 4-rnethy-7-styrylcoumarin are known to crystallize in reactive crystal modifications. In these cases, only mono-cycloaddition occurs either at the pyrone double bond or at the styrenic double bond; see (a) Moorthy, J. N.; Venkatesan, K. Bull. Chem. Soc. Jpn. 1994, 67, 1.
57. (b) J. N. Moorthy, S. D. Samant, K. Venkatesan, J. Chem. Soc. Perkin Trans. 1994, 2, 1223.
58. (c) Vishnumurthy, K.; Guru, Row, T. N.; Venkatesan, K. Photochem. Photobiol. Sci. 2002, 1, 799.
59. (a) Hasegawa, M.; Kato, S.; Yonezawa, N.; Saigo, K. J. Polym. Sci., Polym. Lett. Ed. 1986, 24, 153.
60. (b) Hasegawa, M.; Harashina, H.; Kato, S.; Saigo, K. Macromolecules 1986, 19, 1276.
61. (c) Hasegawa, M.; Chung, C. M.; Muro, N.; Mayekawa, Y. J. Am. Chem. Soc. 1990, 112, 5676.
62. For CSD account of structures with multiple Z′, see Steed, J. W. Cryst. Eng. Comm. 2003, 5, 169.
63. (a) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441.
64. (b) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290.
65. (c) Sarma, J. A. R. P.; Desiraju, G. R. Acc. Chem. Res. 1986, 19, 222.
66. Desiraju, G. R.; Steiner, T. The Weak Hydrogen bond in Structural Chemistry and Biology, Oxford University Press: Oxford. UK, 1999.
67. SHELX-97; Sheldrick, G. M. Program for the Solution and Refinement of Crystal Structures; University of Göttingen, Göttingen, Germany, 1997.