Substituent effects on the bridging modes of photochemical rearrangements of pyrazino-, quinoxalino-, and benzoquinoxalinobarrelenes

Tetrahedron

Volumn 64, Issue 37, 2008, Pages 8907-8921

  Chen, Ann Cheng ^a   Lin, Sheng Yunn ^a   Villarante, Nelson R ^b   Chuang, Gary J ^a   Wu, Te Chun ^a   Liao, Chun Chen ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b UNIVERSITY OF THE PHILIPPINES MANILA   (Philippines)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BENZOQUINOXALINOBARRELENE; PYRAZINOBARRELENE; QUINOXALINOBARRELENE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; IRRADIATION; PHOTOCHEMISTRY; PHOTOREACTIVITY; PRIORITY JOURNAL;

EID: 48049119943     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.054     Document Type: Article

References (74)

1. Liao C.-C., and Peddinti R.K. In: Horspool W.M., and Lenci F. (Eds). Handbook of Photochemistry and Photobiology (2004), CRC, London Chapter 32, p 1
2. Frutos L.M., Sancho U., and Castaño O. Org. Lett. 6 (2004) 1229
3. Zimmerman H.E., and Armesto D. Chem. Rev. 96 (1996) 3065
4. Liao C.-C., and Yang P.-H. In: Horspool W.M., and Song P.-S. (Eds). Handbook of Photochemistry and Photobiology (1995), CRC, London Chapter 15
5. Chen J., Scheffer J.R., and Trotter J. Tetrahedron 48 (1992) 3251
6. Zimmerman H.E. In: Padwa A. (Ed). Organic Photochemistry Vol. 11 (1991), Marcel Dekker, New York, NY 1-36
7. Zimmerman H.E. In: de Mayo P. (Ed). Rearrangements in Ground and Excited States Vol. 3 (1980), Academic, New York, NY 131-166
8. Zimmerman H.E., Amick D.A., and Hemetsberger H. J. Am. Chem. Soc. 95 (1973) 4606
9. Zimmerman H.E., and Bender C.O. J. Am. Chem. Soc. 92 (1970) 4366
10. Zimmerman H.E., and Bender C.O. J. Am. Chem. Soc. 91 (1969) 7516
11. Zimmerman H.E., Givens R.S., and Pagni R.M. J. Am. Chem. Soc. 90 (1968) 6096
12. Zimmerman H.E., Givens R.S., and Pagni R.M. J. Am. Chem. Soc. 90 (1968) 4191
13. Jones R., Scheffer J.R., Trotter J., and Yap M. Tetrahedron Lett. 34 (1993) 31
14. Rattray G., Yang J., Gudmundsdottir A.D., and Scheffer J.R. Tetrahedron Lett. 34 (1993) 35
15. Chen J., Pokkuluri P.R., Scheffer J.R., and Trotter J. J. Photochem. Photobiol. A: Chem. 57 (1991) 21
16. Pokkuluri P.R., Scheffer J.R., and Trotter J. J. Am. Chem. Soc. 112 (1990) 3676
17. Bender C.O., Brooks D.W., Cheng W., Dolman D., O'Shea S.F., and Shugarman S.S. Can. J. Chem. 56 (1978) 3027
18. Bender C.O., and Wilson J. Helv. Chim. Acta 59 (1976) 1469
19. Bender C.O., and O'Shea S.F. Can. J. Chem. 57 (1979) 2804
20. Hemetsberger H., and Nobbe M. Tetrahedron 44 (1988) 67
21. Ramaiah D., Sajimon M.C., Joseph J., and George M.V. Chem. Soc. Rev. 34 (2005) 48
22. Sajimon M., Ramaiah C.D., Kumar S.A., Rath N.P., and George M.V. Tetrahedron 56 (2000) 5421
23. Iwamura M., Tukada H., and Iwamura H. Tetrahedron Lett. 21 (1980) 4865
24. Paddick R.G., Richards K.E., and Wright G.J. Aust. J. Chem. 29 (1976) 1005
25. Chou C.-H., Peddinti R.K., and Liao C.-C. Heterocycles 54 (2001) 61
26. Lin S.-Y., Hsieh H.-P., Peddinti R.K., and Liao C.-C. Tetrahedron Lett. 44 (2003) 8761
27. Liao C.-C., Lin S.-Y., Hsieh H.-P., and Yang P.-H. J. Chin. Chem. Soc. 39 (1992) 275
28. Liao C.-C., and Yang P.-H. J. Chem. Soc., Chem. Commun. (1991) 626
29. Liao C.-C., Hsieh H.-P., and Lin S.-Y. J. Chem. Soc., Chem. Commun. (1990) 545
30. Srinivasan K.G., and Boyer J.H. J. Chem. Soc., Chem. Commun. (1974) 1026
31. Nair V., Anilkumar G., Prabhakaran J., Maliakal D., Eigendorf G.K., and Williard P.G. J. Photochem. Photobiol. A: Chem. 111 (1997) 57
32. Chen A.-C., Chuang G.J., Villarante N.R., and Liao C.-C. J. Org. Chem. 72 (2007) 9690
33. Armesto D. In: Horspool W.M., and Song P.-S. (Eds). Handbook of Photochemistry and Photobiology (1995), CRC, Boca Raton, FL Chapter 73
34. Zimmerman H.E. In: Horspool W.M., and Song P.-S. (Eds). Handbook of Photochemistry and Photobiology (1995), CRC, Boca Raton, FL Chapter 14
35. De Lucchi O., and Adam W. In: Trost B.M., Fleming I., and Paquette L.A. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford Chapter 2.5
36. Liao C.-C., and Lin H.S. J. Chin. Chem. Soc. 30 (1983) 69
37. Chittimala S.K., Shiao H.-Y., and Liao C.-C. Org. Biomol. Chem. 4 (2006) 2267
38. Zimmerman H.E., and Grunewald G.L. J. Am. Chem. Soc. 88 (1966) 183
39. Saito K., and Mukai T. Bull. Chem. Soc. Jpn. 48 (1975) 2334
40. Cristol S.J., Kaufman R.L., Opitz S.M., Szalecki W., and Bindel T.H. J. Am. Chem. Soc. 105 (1983) 3226
41. Ciganek E. J. Am. Chem. Soc. 88 (1966) 2882
42. Ihmels H., Mohrschladt C.J., Grimme J.W., and Quast H. Synthesis (2001) 1175
43. Pan Y., Sheng Z., Ye X., Ao Z., Chu G., Dai J., and Yu S. J. Photchem. Photobiol. A: Chem. 174 (2005) 98
44. Shim S.C., Kim M.S., Lee K.T., Jeong B.M., and Lee B.H. J. Photchem. Photobiol. A: Chem. 65 (1992) 121
45. Fischer G. Chem. Phys. Lett. 33 (1975) 459
46. Boldridge D.W., Scott G.W., and Spiglanin T.A. J. Phys. Chem. 86 (1982) 1976
47. Yamazaki I., Murao T., Yamanaka T., and Yoshihara K. Faraday Discuss. Chem. Soc. 75 (1983) 395
48. Madej S.L., Gillispie G.D., and Lim E.C. Chem. Phys. 32 (1978) 1
49. Zimmerman H.E., and Viriot-Villaume M.-L. J. Am. Chem. Soc. 95 (1973) 1274
50. Evan D.F. J. Chem. Soc. (1960) 1735
51. Murov S.L. Handbook of Photochemistry (1973), Morcel Dekker, New York, NY p 3
52. Evan D.F. J. Chem. Soc. (1957) 1351
53. Tian H., and Yang S. J. Photochem. Photobiol. C: Photochem. Rev. 3 (2002) 67
54. Sevy E.T., Muyskens M.A., Rubin S.M., Flynn G.W., and Muckerman J.T. J. Chem. Phys. 112 (2000) 5829
55. Speier S. Chem. Rev. 96 (1996) 1953
56. Morrison H. Acc. Chem. Res. 12 (1979) 383
57. Zimmerman H.E., and Amick D.R. J. Am. Chem. Soc. 95 (1973) 3977
58. Altundas R., Dastan A., Ünalde N.S., Güven K., Uzun O., and Balci M. Eur. J. Org. Chem. (2002) 526
59. Sajimon M.C., Ramaiah D., Muneer M., Ajithkumar E.S., Rath N.P., and George M.V. J. Org. Chem. 64 (1999) 6347
60. Chen J., Pokkuluri P.R., Scheffer J.R., and Trotter J. Acta Crystallogr. B49 (1993) 905
61. Ku Y.A., Paquette L.A., Rozeboom M.D., and Houk K.N. J. Am. Chem. Soc. 101 (1979) 5981
62. Paquette L.A., Cottrell D.M., Snow R.A., Gifkins K.B., and Clardy J. J. Am. Chem. Soc. 97 (1975) 3275
63. Chang S.-Y., Huang S.-L., Villarante N.R., and Liao C.-C. Eur. J. Org. Chem. (2006) 4648
64. Zimmerman H.E., Sulzbach H.M., and Tollefson M.B. J. Am. Chem. Soc. 115 (1993) 6548
65. Loufty R.O., and Louft R.O. Can. J. Chem. 54 (1976) 1454
66. Crowly K. J. Proc. Chem. Soc. (1966) 245
67. Glass R.W., Robertson L.C., and Merrit J.A. J. Chem. Phys. 53 (1970) 3857
68. Jordan A.D., Fischer G., Rokos K., and Ross I.G. J. Mol. Spectrosc. 45 (1973) 173
69. Hadley S.G. J. Phys. Chem. 75 (1971) 2083
70. Yajima Y., and Lim E.C. Chem. Phys. Lett. 73 (1980) 249
71. Hoffmann R.W., Hauel N., and Frickel F. Angew. Chem., Int. Ed. Engl. 16 (1977) 475
72. James D.R., Birnberg G.H., and Paquette L.A. J. Am. Chem. Soc. 96 (1974) 7465
73. Guldi D.M., Torres-Garcia G., and Mattay J. J. Phys. Chem. A 102 (1998) 9679
74. Behr J., Braun R., Martin H.-D., Rubin M.B., and Steigel A. Chem. Ber. 124 (1991) 815