Phototransformations of bridgehead-substituted dibenzobarrelenes. Steady state and laser flash photolysis studies of 9-benzoyl- and 9-(α-hydroxybenzyl)-substituted dibenzobarrelenes

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 103, Issue 1-2, 1997, Pages 69-73

  Kumar, S Ajaya ^a   Ramaiah, D ^a   Eldho, N V ^a   Das, Suresh ^a   Rath, N P ^b   George, M V ^a,c  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b UNIVERSITY OF MISSOURI ST LOUIS   (United States)

^c UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

Dibenzobarrelenes; Laser flash photolysis; Phototransformations; Steady state photolysis

Indexed keywords

EID: 0031565220     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1010-6030(96)04489-9     Document Type: Article

References (22)

1. [1] C.V. Kumar, B.A.R.C. Murty, S. Lahiri, E. Chackachery, J.C. Scaiano and M.V. George, J. Org. Chem., 49 (1984) 4923-4929.
2. [2] S. Pratapan, K. Ashok, K.R. Gopidas, N.P. Rath, P.K. Das and M.V. George, J. Org. Chem., 55 (1990) 1304-1308.
3. [3] B.A.R.C. Murty, S. Pratapan, C.V. Kumar, P.K. Das and M.V. George, J. Org. Chem., 50 (1985) 2533-2538. S. Pratapan, K. Ashok, D.R. Cyr, P.K. Das and M.V. George, J. Org. Chem., 52 (1987) 5512-5517. J.R. Scheffer, J. Trotter, M. Garcia-Garibay and F. Wireko, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 156 (1988) 63-84. M. Garcia-Garibay, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 111 (1989) 4985-4986. P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 112 (1990) 3676-3677. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, Tetrahedron Lett., 31 (1990) 6803-6806. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Photochem. Photobiol. A: Chem., 57 (1991) 21-26. C.V. Asokan, S.A. Kumar, S. Das, N.P. Rath and M.V. George, J. Org. Chem., 56 (1991) 5890-5893. R. Jones, J.R. Scheffer, J. Trotter and M. Yap, Tetrahedron Lett., 34 (1993) 31-34. G. Rattray, J. Yang, A.D. Gudmundsdottir and J.R. Scheffer, Tetrahedron Lett., 34 (1993) 35-38. S.A. Kumar, C.V. Asokan, S. Das, J.A. Wilbur, N.P. Rath and M.V. George, J. Photochem. Photobiol. A: Chem., 71 (1993) 27-31.
4. [3] B.A.R.C. Murty, S. Pratapan, C.V. Kumar, P.K. Das and M.V. George, J. Org. Chem., 50 (1985) 2533-2538. S. Pratapan, K. Ashok, D.R. Cyr, P.K. Das and M.V. George, J. Org. Chem., 52 (1987) 5512-5517. J.R. Scheffer, J. Trotter, M. Garcia-Garibay and F. Wireko, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 156 (1988) 63-84. M. Garcia-Garibay, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 111 (1989) 4985-4986. P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 112 (1990) 3676-3677. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, Tetrahedron Lett., 31 (1990) 6803-6806. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Photochem. Photobiol. A: Chem., 57 (1991) 21-26. C.V. Asokan, S.A. Kumar, S. Das, N.P. Rath and M.V. George, J. Org. Chem., 56 (1991) 5890-5893. R. Jones, J.R. Scheffer, J. Trotter and M. Yap, Tetrahedron Lett., 34 (1993) 31-34. G. Rattray, J. Yang, A.D. Gudmundsdottir and J.R. Scheffer, Tetrahedron Lett., 34 (1993) 35-38. S.A. Kumar, C.V. Asokan, S. Das, J.A. Wilbur, N.P. Rath and M.V. George, J. Photochem. Photobiol. A: Chem., 71 (1993) 27-31.
5. [3] B.A.R.C. Murty, S. Pratapan, C.V. Kumar, P.K. Das and M.V. George, J. Org. Chem., 50 (1985) 2533-2538. S. Pratapan, K. Ashok, D.R. Cyr, P.K. Das and M.V. George, J. Org. Chem., 52 (1987) 5512-5517. J.R. Scheffer, J. Trotter, M. Garcia-Garibay and F. Wireko, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 156 (1988) 63-84. M. Garcia-Garibay, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 111 (1989) 4985-4986. P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 112 (1990) 3676-3677. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, Tetrahedron Lett., 31 (1990) 6803-6806. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Photochem. Photobiol. A: Chem., 57 (1991) 21-26. C.V. Asokan, S.A. Kumar, S. Das, N.P. Rath and M.V. George, J. Org. Chem., 56 (1991) 5890-5893. R. Jones, J.R. Scheffer, J. Trotter and M. Yap, Tetrahedron Lett., 34 (1993) 31-34. G. Rattray, J. Yang, A.D. Gudmundsdottir and J.R. Scheffer, Tetrahedron Lett., 34 (1993) 35-38. S.A. Kumar, C.V. Asokan, S. Das, J.A. Wilbur, N.P. Rath and M.V. George, J. Photochem. Photobiol. A: Chem., 71 (1993) 27-31.
6. [3] B.A.R.C. Murty, S. Pratapan, C.V. Kumar, P.K. Das and M.V. George, J. Org. Chem., 50 (1985) 2533-2538. S. Pratapan, K. Ashok, D.R. Cyr, P.K. Das and M.V. George, J. Org. Chem., 52 (1987) 5512-5517. J.R. Scheffer, J. Trotter, M. Garcia-Garibay and F. Wireko, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 156 (1988) 63-84. M. Garcia-Garibay, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 111 (1989) 4985-4986. P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 112 (1990) 3676-3677. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, Tetrahedron Lett., 31 (1990) 6803-6806. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Photochem. Photobiol. A: Chem., 57 (1991) 21-26. C.V. Asokan, S.A. Kumar, S. Das, N.P. Rath and M.V. George, J. Org. Chem., 56 (1991) 5890-5893. R. Jones, J.R. Scheffer, J. Trotter and M. Yap, Tetrahedron Lett., 34 (1993) 31-34. G. Rattray, J. Yang, A.D. Gudmundsdottir and J.R. Scheffer, Tetrahedron Lett., 34 (1993) 35-38. S.A. Kumar, C.V. Asokan, S. Das, J.A. Wilbur, N.P. Rath and M.V. George, J. Photochem. Photobiol. A: Chem., 71 (1993) 27-31.
7. [3] B.A.R.C. Murty, S. Pratapan, C.V. Kumar, P.K. Das and M.V. George, J. Org. Chem., 50 (1985) 2533-2538. S. Pratapan, K. Ashok, D.R. Cyr, P.K. Das and M.V. George, J. Org. Chem., 52 (1987) 5512-5517. J.R. Scheffer, J. Trotter, M. Garcia-Garibay and F. Wireko, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 156 (1988) 63-84. M. Garcia-Garibay, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 111 (1989) 4985-4986. P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 112 (1990) 3676-3677. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, Tetrahedron Lett., 31 (1990) 6803-6806. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Photochem. Photobiol. A: Chem., 57 (1991) 21-26. C.V. Asokan, S.A. Kumar, S. Das, N.P. Rath and M.V. George, J. Org. Chem., 56 (1991) 5890-5893. R. Jones, J.R. Scheffer, J. Trotter and M. Yap, Tetrahedron Lett., 34 (1993) 31-34. G. Rattray, J. Yang, A.D. Gudmundsdottir and J.R. Scheffer, Tetrahedron Lett., 34 (1993) 35-38. S.A. Kumar, C.V. Asokan, S. Das, J.A. Wilbur, N.P. Rath and M.V. George, J. Photochem. Photobiol. A: Chem., 71 (1993) 27-31.
8. [3] B.A.R.C. Murty, S. Pratapan, C.V. Kumar, P.K. Das and M.V. George, J. Org. Chem., 50 (1985) 2533-2538. S. Pratapan, K. Ashok, D.R. Cyr, P.K. Das and M.V. George, J. Org. Chem., 52 (1987) 5512-5517. J.R. Scheffer, J. Trotter, M. Garcia-Garibay and F. Wireko, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 156 (1988) 63-84. M. Garcia-Garibay, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 111 (1989) 4985-4986. P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 112 (1990) 3676-3677. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, Tetrahedron Lett., 31 (1990) 6803-6806. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Photochem. Photobiol. A: Chem., 57 (1991) 21-26. C.V. Asokan, S.A. Kumar, S. Das, N.P. Rath and M.V. George, J. Org. Chem., 56 (1991) 5890-5893. R. Jones, J.R. Scheffer, J. Trotter and M. Yap, Tetrahedron Lett., 34 (1993) 31-34. G. Rattray, J. Yang, A.D. Gudmundsdottir and J.R. Scheffer, Tetrahedron Lett., 34 (1993) 35-38. S.A. Kumar, C.V. Asokan, S. Das, J.A. Wilbur, N.P. Rath and M.V. George, J. Photochem. Photobiol. A: Chem., 71 (1993) 27-31.
9. [3] B.A.R.C. Murty, S. Pratapan, C.V. Kumar, P.K. Das and M.V. George, J. Org. Chem., 50 (1985) 2533-2538. S. Pratapan, K. Ashok, D.R. Cyr, P.K. Das and M.V. George, J. Org. Chem., 52 (1987) 5512-5517. J.R. Scheffer, J. Trotter, M. Garcia-Garibay and F. Wireko, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 156 (1988) 63-84. M. Garcia-Garibay, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 111 (1989) 4985-4986. P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 112 (1990) 3676-3677. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, Tetrahedron Lett., 31 (1990) 6803-6806. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Photochem. Photobiol. A: Chem., 57 (1991) 21-26. C.V. Asokan, S.A. Kumar, S. Das, N.P. Rath and M.V. George, J. Org. Chem., 56 (1991) 5890-5893. R. Jones, J.R. Scheffer, J. Trotter and M. Yap, Tetrahedron Lett., 34 (1993) 31-34. G. Rattray, J. Yang, A.D. Gudmundsdottir and J.R. Scheffer, Tetrahedron Lett., 34 (1993) 35-38. S.A. Kumar, C.V. Asokan, S. Das, J.A. Wilbur, N.P. Rath and M.V. George, J. Photochem. Photobiol. A: Chem., 71 (1993) 27-31.
10. [3] B.A.R.C. Murty, S. Pratapan, C.V. Kumar, P.K. Das and M.V. George, J. Org. Chem., 50 (1985) 2533-2538. S. Pratapan, K. Ashok, D.R. Cyr, P.K. Das and M.V. George, J. Org. Chem., 52 (1987) 5512-5517. J.R. Scheffer, J. Trotter, M. Garcia-Garibay and F. Wireko, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 156 (1988) 63-84. M. Garcia-Garibay, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 111 (1989) 4985-4986. P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 112 (1990) 3676-3677. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, Tetrahedron Lett., 31 (1990) 6803-6806. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Photochem. Photobiol. A: Chem., 57 (1991) 21-26. C.V. Asokan, S.A. Kumar, S. Das, N.P. Rath and M.V. George, J. Org. Chem., 56 (1991) 5890-5893. R. Jones, J.R. Scheffer, J. Trotter and M. Yap, Tetrahedron Lett., 34 (1993) 31-34. G. Rattray, J. Yang, A.D. Gudmundsdottir and J.R. Scheffer, Tetrahedron Lett., 34 (1993) 35-38. S.A. Kumar, C.V. Asokan, S. Das, J.A. Wilbur, N.P. Rath and M.V. George, J. Photochem. Photobiol. A: Chem., 71 (1993) 27-31.
11. [3] B.A.R.C. Murty, S. Pratapan, C.V. Kumar, P.K. Das and M.V. George, J. Org. Chem., 50 (1985) 2533-2538. S. Pratapan, K. Ashok, D.R. Cyr, P.K. Das and M.V. George, J. Org. Chem., 52 (1987) 5512-5517. J.R. Scheffer, J. Trotter, M. Garcia-Garibay and F. Wireko, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 156 (1988) 63-84. M. Garcia-Garibay, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 111 (1989) 4985-4986. P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 112 (1990) 3676-3677. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, Tetrahedron Lett., 31 (1990) 6803-6806. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Photochem. Photobiol. A: Chem., 57 (1991) 21-26. C.V. Asokan, S.A. Kumar, S. Das, N.P. Rath and M.V. George, J. Org. Chem., 56 (1991) 5890-5893. R. Jones, J.R. Scheffer, J. Trotter and M. Yap, Tetrahedron Lett., 34 (1993) 31-34. G. Rattray, J. Yang, A.D. Gudmundsdottir and J.R. Scheffer, Tetrahedron Lett., 34 (1993) 35-38. S.A. Kumar, C.V. Asokan, S. Das, J.A. Wilbur, N.P. Rath and M.V. George, J. Photochem. Photobiol. A: Chem., 71 (1993) 27-31.
12. [3] B.A.R.C. Murty, S. Pratapan, C.V. Kumar, P.K. Das and M.V. George, J. Org. Chem., 50 (1985) 2533-2538. S. Pratapan, K. Ashok, D.R. Cyr, P.K. Das and M.V. George, J. Org. Chem., 52 (1987) 5512-5517. J.R. Scheffer, J. Trotter, M. Garcia-Garibay and F. Wireko, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 156 (1988) 63-84. M. Garcia-Garibay, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 111 (1989) 4985-4986. P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 112 (1990) 3676-3677. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, Tetrahedron Lett., 31 (1990) 6803-6806. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Photochem. Photobiol. A: Chem., 57 (1991) 21-26. C.V. Asokan, S.A. Kumar, S. Das, N.P. Rath and M.V. George, J. Org. Chem., 56 (1991) 5890-5893. R. Jones, J.R. Scheffer, J. Trotter and M. Yap, Tetrahedron Lett., 34 (1993) 31-34. G. Rattray, J. Yang, A.D. Gudmundsdottir and J.R. Scheffer, Tetrahedron Lett., 34 (1993) 35-38. S.A. Kumar, C.V. Asokan, S. Das, J.A. Wilbur, N.P. Rath and M.V. George, J. Photochem. Photobiol. A: Chem., 71 (1993) 27-31.
13. [3] B.A.R.C. Murty, S. Pratapan, C.V. Kumar, P.K. Das and M.V. George, J. Org. Chem., 50 (1985) 2533-2538. S. Pratapan, K. Ashok, D.R. Cyr, P.K. Das and M.V. George, J. Org. Chem., 52 (1987) 5512-5517. J.R. Scheffer, J. Trotter, M. Garcia-Garibay and F. Wireko, Mol. Cryst. Liq. Cryst. Inc. Nonlin. Opt., 156 (1988) 63-84. M. Garcia-Garibay, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 111 (1989) 4985-4986. P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Am. Chem. Soc., 112 (1990) 3676-3677. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, Tetrahedron Lett., 31 (1990) 6803-6806. J. Chen, P.R. Pokkuluri, J.R. Scheffer and J. Trotter, J. Photochem. Photobiol. A: Chem., 57 (1991) 21-26. C.V. Asokan, S.A. Kumar, S. Das, N.P. Rath and M.V. George, J. Org. Chem., 56 (1991) 5890-5893. R. Jones, J.R. Scheffer, J. Trotter and M. Yap, Tetrahedron Lett., 34 (1993) 31-34. G. Rattray, J. Yang, A.D. Gudmundsdottir and J.R. Scheffer, Tetrahedron Lett., 34 (1993) 35-38. S.A. Kumar, C.V. Asokan, S. Das, J.A. Wilbur, N.P. Rath and M.V. George, J. Photochem. Photobiol. A: Chem., 71 (1993) 27-31.
14. [4] R.E. Lutz, in E.C. Horning (ed.), Organic Synthesis, Collect. Vol. 3, Wiley, New York, 1995, pp. 248-250. R.E. Lutz and W.R. Smithey, Jr., J. Org. Chem., 16 (1951) 51-56.
15. [4] R.E. Lutz, in E.C. Horning (ed.), Organic Synthesis, Collect. Vol. 3, Wiley, New York, 1995, pp. 248-250. R.E. Lutz and W.R. Smithey, Jr., J. Org. Chem., 16 (1951) 51-56.
16. [5] A.I. Bokava and I.K. Buchina, Zh. Org. Khim., 20 (1984) 1318-1321.
17. [6] S. Gibson, A.D. Mosnaim, D.C. Nonheble and J.A. Russel, Tetrahedron, 25 (1969) 5047-5057.
18. [7] G.M. Sheldrick, SHELX-TL, Siemens Analytical X-Ray Division, Madison, WI, 1991.
19. [8] P.K. Das, M.V. Encinas, R.D. Small, Jr. and J.C. Scaiano, J. Am. Chem. Soc., 101 (1979) 6965-6970.
20. [9] V. Nagarajan and R.W. Fessenden, J. Phys. Chem., 89 (1985) 2330-2335.
21. [10] D. Ramaiah, N.V. Ajaya Kumar, S. Das, N.P. Rath and M.V. George, Acta Crystallogr. Sect. C, in press.
22. [11] C.V. Kumar, L. Quin and P.K. Das, J. Chem. Soc., Faraday Trans. 2, 80 (1984) 783-793.