Phototransformations of bridgehead-disubstituted dibenzobarrelenes. Interesting rearrangements of dibenzosemibullvalene intermediates derived from 9-(hydroxyalkyl)-10-methoxy-substituted dibenzobarrelenes

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5468-5473

  Ramaiah, D ^a   Kumar, S A ^a   Asokan, C V ^a,d   Mathew, T ^a   Das, S ^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)

^d MAHATMA GANDHI UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000687494     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952046u     Document Type: Article

References (31)

1. (a) For some recent reviews on the photochemistry of dibenzo-barrelenes and the general di-π-methane rearrangement, see: (a) Zimmerman, H. E. In Rearrangement in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Vol. 3, Chapter 16, pp 131-166. (b) Zimmerman, H. E. In Organic Photochemistry; Padwa, A., Ed.; Marcell Dekker: New York, 1991; Vol. 11, pp 1-36. (c) Scheffer, J. R.; Pokkuluri, P. R. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991; pp 185-246. (d) de Lucchi, O.; Adam, W. In ComprehensiveOrganic Synthesis; Trost, B. M., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 193-214. (e) Chen, J.; Scheffer, J. R.; Trotter, J. Tetrahedron 1992, 48, 3251-3274. (f) Zimmerman, H. E.; Sulzbach, H. M.; Tollefson, M. B. J. Am. Chem Soc. 1993, 115, 6548-6556. (g) Scheffer, J. R.; Yang, J. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P. S., Eds.; CRC Press: Boca Raton, FL, 1995; Chapter 16, pp 204-221.
2. (a) For some recent reviews on the photochemistry of dibenzo-barrelenes and the general di-π-methane rearrangement, see: (a) Zimmerman, H. E. In Rearrangement in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Vol. 3, Chapter 16, pp 131-166. (b) Zimmerman, H. E. In Organic Photochemistry; Padwa, A., Ed.; Marcell Dekker: New York, 1991; Vol. 11, pp 1-36. (c) Scheffer, J. R.; Pokkuluri, P. R. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991; pp 185-246. (d) de Lucchi, O.; Adam, W. In ComprehensiveOrganic Synthesis; Trost, B. M., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 193-214. (e) Chen, J.; Scheffer, J. R.; Trotter, J. Tetrahedron 1992, 48, 3251-3274. (f) Zimmerman, H. E.; Sulzbach, H. M.; Tollefson, M. B. J. Am. Chem Soc. 1993, 115, 6548-6556. (g) Scheffer, J. R.; Yang, J. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P. S., Eds.; CRC Press: Boca Raton, FL, 1995; Chapter 16, pp 204-221.
3. (a) For some recent reviews on the photochemistry of dibenzo-barrelenes and the general di-π-methane rearrangement, see: (a) Zimmerman, H. E. In Rearrangement in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Vol. 3, Chapter 16, pp 131-166. (b) Zimmerman, H. E. In Organic Photochemistry; Padwa, A., Ed.; Marcell Dekker: New York, 1991; Vol. 11, pp 1-36. (c) Scheffer, J. R.; Pokkuluri, P. R. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991; pp 185-246. (d) de Lucchi, O.; Adam, W. In ComprehensiveOrganic Synthesis; Trost, B. M., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 193-214. (e) Chen, J.; Scheffer, J. R.; Trotter, J. Tetrahedron 1992, 48, 3251-3274. (f) Zimmerman, H. E.; Sulzbach, H. M.; Tollefson, M. B. J. Am. Chem Soc. 1993, 115, 6548-6556. (g) Scheffer, J. R.; Yang, J. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P. S., Eds.; CRC Press: Boca Raton, FL, 1995; Chapter 16, pp 204-221.
4. (a) For some recent reviews on the photochemistry of dibenzo-barrelenes and the general di-π-methane rearrangement, see: (a) Zimmerman, H. E. In Rearrangement in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Vol. 3, Chapter 16, pp 131-166. (b) Zimmerman, H. E. In Organic Photochemistry; Padwa, A., Ed.; Marcell Dekker: New York, 1991; Vol. 11, pp 1-36. (c) Scheffer, J. R.; Pokkuluri, P. R. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991; pp 185-246. (d) de Lucchi, O.; Adam, W. In ComprehensiveOrganic Synthesis; Trost, B. M., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 193-214. (e) Chen, J.; Scheffer, J. R.; Trotter, J. Tetrahedron 1992, 48, 3251-3274. (f) Zimmerman, H. E.; Sulzbach, H. M.; Tollefson, M. B. J. Am. Chem Soc. 1993, 115, 6548-6556. (g) Scheffer, J. R.; Yang, J. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P. S., Eds.; CRC Press: Boca Raton, FL, 1995; Chapter 16, pp 204-221.
5. (a) For some recent reviews on the photochemistry of dibenzo-barrelenes and the general di-π-methane rearrangement, see: (a) Zimmerman, H. E. In Rearrangement in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Vol. 3, Chapter 16, pp 131-166. (b) Zimmerman, H. E. In Organic Photochemistry; Padwa, A., Ed.; Marcell Dekker: New York, 1991; Vol. 11, pp 1-36. (c) Scheffer, J. R.; Pokkuluri, P. R. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991; pp 185-246. (d) de Lucchi, O.; Adam, W. In ComprehensiveOrganic Synthesis; Trost, B. M., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 193-214. (e) Chen, J.; Scheffer, J. R.; Trotter, J. Tetrahedron 1992, 48, 3251-3274. (f) Zimmerman, H. E.; Sulzbach, H. M.; Tollefson, M. B. J. Am. Chem Soc. 1993, 115, 6548-6556. (g) Scheffer, J. R.; Yang, J. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P. S., Eds.; CRC Press: Boca Raton, FL, 1995; Chapter 16, pp 204-221.
6. (a) For some recent reviews on the photochemistry of dibenzo-barrelenes and the general di-π-methane rearrangement, see: (a) Zimmerman, H. E. In Rearrangement in Ground and Excited States; de Mayo, P., Ed.; Academic: New York, 1980; Vol. 3, Chapter 16, pp 131-166. (b) Zimmerman, H. E. In Organic Photochemistry; Padwa, A., Ed.; Marcell Dekker: New York, 1991; Vol. 11, pp 1-36. (c) Scheffer, J. R.; Pokkuluri, P. R. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: New York, 1991; pp 185-246. (d) de Lucchi, O.; Adam, W. In ComprehensiveOrganic Synthesis; Trost, B. M., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 193-214. (e) Chen, J.; Scheffer, J. R.; Trotter, J. Tetrahedron 1992, 48, 3251-3274. (f) Zimmerman, H. E.; Sulzbach, H. M.; Tollefson, M. B. J. Am. Chem Soc. 1993, 115, 6548-6556. (g) Scheffer, J. R.; Yang, J. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P. S., Eds.; CRC Press: Boca Raton, FL, 1995; Chapter 16, pp 204-221.
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