Substituent effects on regioselectivity in the photorearrangement of a few naphthobarrelenes

Tetrahedron

Volumn 56, Issue 30, 2000, Pages 5421-5428

  Sajimon, Meledathu C ^a   Ramaiah, Danaboyina ^a   Ajaya Kumar, S ^a   Rath, Nigam P ^b   George, Manapurathu V ^a,c  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b UNIVERSITY OF MISSOURI ST LOUIS   (United States)

^c JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

Di methane rearrangement; Naphthobarrelenes; Naphthosemibullvalenes; Regioselectivity

Indexed keywords

FURAN DERIVATIVE; NAPHTHALENE DERIVATIVE; NAPHTHOBABARRELENE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; MOLECULAR STABILITY; PHOTOCHEMISTRY; PRIORITY JOURNAL; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 0034698185     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00450-6     Document Type: Article

References (38)

1. Contribution No. RRLT-PRU-120 from the Regional Research Laboratory (CSIR), Trivandrum, India.
2. For some recent reviews on the di-π-methane rearrangement of barrelenes see: (a) Zimmerman, H. E. In Rearrangements 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 Comprehensive Organic Synthesis; Trost, B. M., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 193-214.
3. For some recent reviews on the di-π-methane rearrangement of barrelenes see: (a) Zimmerman, H. E. In Rearrangements 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 Comprehensive Organic Synthesis; Trost, B. M., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 193-214.
4. For some recent reviews on the di-π-methane rearrangement of barrelenes see: (a) Zimmerman, H. E. In Rearrangements 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 Comprehensive Organic Synthesis; Trost, B. M., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 193-214.
5. For some recent reviews on the di-π-methane rearrangement of barrelenes see: (a) Zimmerman, H. E. In Rearrangements 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 Comprehensive Organic Synthesis; Trost, B. M., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 193-214.
6. (a) Zimmerman, H. E.; Givens, R. S.; Pagni, R. M. J. Am. Chem. Soc. 1968, 90, 4191-4193.
7. (b) Zimmerman, H. E.; Givens, R. S.; Pagni, R. M. J. Am. Chem. Soc. 1968, 90, 6096-6108.
8. (c) Brewers, J. P. N.; Heaney, H. J. J. Chem. Soc. Chem. Commun. 1967, 811-812.
9. (d) Bender, C. O.; Brooks, D. W.; Cheng, W.; Dolman, D.; O'Shea, S. F.; Sugaeman, S. Can. J. Chem. 1979, 56, 3027-3037.
10. (e) Bender, C. O.; Bengton, D. L.; Dolman, D.; Herle, L. E. L.; O'Shea, S. F. Can. J. Chem. 1982, 60, 1942-1952.
11. (a) Chen, J.; Scheffer, J. R.; Trotter, J. Tetrahedron 1992, 48, 3251-3274.
12. (b) Zimmerman, H. E; Sulzbach, H. M.; Tollefson, M. B. J. Am. Chem. Soc. 1993, 115, 6548-6556.
13. (c) Scheffer, J. R.; Yang, J. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P. S., Eds.; CRC: Boca Raton, FL, 1995; Chapter 16, pp 204-221.
14. (a) Zimmerman, H. E.; Bender, C. O. J. Am. Chem. Soc. 1969, 91, 7516-7518.
15. (b) Zimmerman, H. E.; Bender, C. O. J. Am. Chem. Soc. 1970, 92, 4366-4376.
16. (c) Bender, C. O.; Elder, J. L. M.; Herbst, A. J.; Miller, L. E. Can. J. Chem. 1972, 50, 395-401.
17. (d) Zimmerman, H. E.; Viriot-Villaume, M. L. J. Am. Chem. Soc. 1973, 95, 1274-1280.
18. (e) Zimmerman, H. E.; Kutateladze, A. G.; Mackawa, Y.; Mangette, J. E. J. Am. Chem. Soc. 1994, 116, 9795-9796.
19. (a) Ciganek, E. J. Am. Chem. Soc. 1966, 88, 2882-2883.
20. (b) Rabideau, P. W.; Hamilton, J. B.; Friedmann, L. J. Am. Chem. Soc. 1968, 90, 4465-4465.
21. (c) Zimmerman, H. E.; Grunewald, G. L. J. Am. Chem. Soc. 1966, 88, 183-184.
22. Sajimon M.C., Ramaiah D., Muneer M., Ajithkumar E.S., Rath N.P., George M.V. J. Org. Chem. 64:1999;6347-6352.
23. Zimmerman H.E., Amick D.R., Hemetsberger. J. Am. Chem. Soc. 95:1973;4606-4610.
24. Pratapan S., Ashok K., Gopidas K.R., Rath N.P., Das P.K., George M.V. J. Org. Chem. 55:1990;1304-1308.
25. (a) Sheldrick, G. M. Siemens Analytical X-ray Division, Madison, WI, 1991.
26. (b) CCDC Nos. 10a (Compound No. in the text): 143874; 10b: 143875; 12e: 143872; 14b: 143873.
27. Rüchardt C. Top. Curr. Chem. 88:1980;1-32.
28. Paquette L.A., Bay E. J. Am. Chem. Soc. 106:1984;6693-6701.
29. Evaluated using AM1 semi-empirical method of PC SPARTAN software obtained from Wavefunction, Inc., 18401 Von Karman, Suite 370, Irvine, CA 92612, USA.
30. Sabacky M.J., Johnson C.S. Jr., Smith R.G., Gutowsky H.S., Martin J.C. J. Am. Chem. Soc. 89:1967;2054.
31. (a) Junjappa, H.; Saxene, M. K.; Ramaiah, D.; Loharay, B. B.; Rath, N. P.; George, M. V. J. Org. Chem. 1998, 63, 9801-9805.
32. (b) Ramaiah, D.; Muneer, M.; Gopidas, K. R.; Das, P. K.; Rath, N. P.; George, M. V. J. Org. Chem. 1996, 61, 4240-4246.
33. (a) Lutz, R. E. In Org. Synth.; Horning, E. C., Ed.; Wiley: New York, 1995; Collect. Vol. 3, pp 248-250.
34. (b) Lutz, R. E.; Smithy Jr., W. R. J. Org. Chem. 1951, 16, 648-654.
35. Bokava A.I., Buchina I.K. Zh. Org. Khim. 20:1984;1318-1321.
36. Krollpfeiffer F., Branschield F., Thorn F., Schneider K. Ann. 462:1928;46-72.
37. Merritt C. Jr., Braun C.E. Rabjohn N. Organic Synthesis. 1967;8-10 Wiley, New York.
38. Gibson S., Mosnaim A.D., Nonhebel D.C., Russel J.A. Tetrahedron. 25:1969;5047.