Solid-State Photochromism and Photoreactivity of o- And p-Anisaldehydes. Remarkable Stabilization of o-Xylylenols

Organic Letters

Volumn 3, Issue 10, 2001, Pages 1579-1582

  Narasimha Moorthy, J ^a   Mal, Prasenjit ^a   Natarajan, R ^a   Venugopalan, P ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b PANJAB UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041837660     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0158720     Document Type: Article

References (30)

1. Sammes, P. G. Tetrahedron 1976, 32, 405.
2. Segura, J. L.; Martin, N. Chem. Rev. 1999, 99, 3199.
3. Das, P. K.; Encinas, M. V.; Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1979, 101, 6965.
4. Haag, R.; Wirz, J.; Wagner, P. J. Helv. Chim. Acta 1977, 60, 2595.
5. For usage of the term "o-xylylenol", see: Wagner, P. J.; Sobczak, M.; Park, B.-S. J. Am. Chem. Soc. 1998, 120, 2488.
6. Wagner, P. J.; Subrahmanyam, D.; Park, B.-S. J. Am. Chem. Soc. 1991, 113, 709.
7. Yang, N. C.; Rivas, C. J. Am. Chem. Soc. 1961, 83, 2213.
8. Zwicker, E. F.; Grossweiner, L. I.; Yang, N. C. J. Am. Chem. Soc. 1963, 85, 2213.
9. Huffman, K. R.; Loy, M.; Ullman, E. F. J. Am. Chem. Soc. 1965, 87, 5417.
10. Gore, P. H.; Hoskins, J. A.; Lott, K. A. K.; Waters, D. N. Photochem. Photobiol. 1970, 11, 551.
11. Kumar, V. A.; Venkatesan, K. J. Chem. Soc., Perkin Trans. 2 1991, 829.
12. Sarkar, T. K.; Ghosh, S. K.; Moorthy, J. N.; Fang, J.-M.; Nandy, S. K.; Sathyamurthy, N.; Chakraborty, D. Tetrahedron Lett. 2000, 41, 6909.
13. For a recent special issue on "Photochromism: Memories and Switches", see: Chem. Rev. 2000, 100, issue 5.
14. Benard, S.; Yo, P. Chem. Commun. 2000, 65 and references therein.
15. For example, mesitaldehyde is known to afford the 1,4-biradical with a quantum yield of 0.84; see ref 3.
16. Gelicki, J. Krantz, A. J. Chem. Soc., Perkin Trans. 2 1984, 1623.
17. 3) δ 16.6, 41.53, 56.46, 68.6, 102.8, 112.8, 133.7, 138.8, 143.5, 156.8.
18. Bromophenyl ketones are known to undergo photoinduced C - Br bond cleavage; see: Wagner, P. J.; Sedon, J. H.; Gudmundsdottir, A. J. Am. Chem. Soc. 1996, 118, 746. Although this process may be competitive in 1b and 2b, we believe that the recombination of the radicals to the precursor aldehydes would be faster in the solid matrix.
19. Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433.
20. Ito, Y. Synthesis 1998, 401.
21. Scheffer, J. R.; Pokkuluri, P. R. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991; Chapter 5, p 185.
22. The solution-state photochemistry of simple o-tolualdehyde is marked by the formation of a variety of products; see: Findlay, D. M.; Tchir, M. F. J. Chem. Soc., Chem. Commun. 1974, 514. Arnold, B. J.; Mellows, S. M.; Sammes, P. G.; Wallace, T. W. J. Chem. Soc., Perkin Trans. 1 1974, 401.
23. The solution-state photochemistry of simple o-tolualdehyde is marked by the formation of a variety of products; see: Findlay, D. M.; Tchir, M. F. J. Chem. Soc., Chem. Commun. 1974, 514. Arnold, B. J.; Mellows, S. M.; Sammes, P. G.; Wallace, T. W. J. Chem. Soc., Perkin Trans. 1 1974, 401.
24. The detailed crystal structure analyses of 1b and 1c will be reported elsewhere.
25. The geometrical parameters for γ-hydrogen abstraction (Ihmels, H.; Scheffer, J. R. Tetrahedron 1999, 55, 885) calculated from X-ray structural parameters fall in the range generally observed. Thus, the γ-hydrogen abstraction, the primary event, is facile for both 1b and 2b.
26. Ito, Y.; Kawatsuki, N.; Giri, B. P.; Yoshida, M.; Matsuura, T. J. Org. Chem. 1985, 50, 2893.
27. Ito, Y.; Kano, G.; Nakamura, N. J. Org. Chem. 1998, 63, 5643.
28. Coll, G.; Costa, A.; Deya, P. M.; Flexas, F.; Rotger, C.; Saa, J. M. J. Org. Chem. 1992, 57, 6222.
29. Dewar, M. J. S.; Zeobish, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3092.
30. Kitaura, Y.; Matsuura, T. Tetrahedron 1971, 27, 1597.