Nafion as an efficient reaction medium for diastereoselective photochemical reactions

Tetrahedron Letters

Volumn 49, Issue 15, 2008, Pages 2461-2465

  Arumugam, Selvanathan ^a  

^a University of Miami   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,2 DIMETHYL 1,2 DIHYDRONAPTHALENONE 4 CARBOXYLIC ACID DERIVATIVE; 2,3 DIPHENYLCYCLOPROPANE 1 CARBOXYLIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; COPOLYMER; NAFION; PERFLUORO 3,6 DIOXA 4 METHYL 7 OCTENE SULFONIC ACID; SULFONIC ACID DERIVATIVE; TETRAFLUOROETHYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; IRRADIATION; ISOMER; PHOTOCHEMISTRY; PHOTOLYSIS; PHOTOREACTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 40649094944     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.041     Document Type: Article

References (61)

1. (a) H. Rau Chem. Rev. 83 1983 535
2. (b) Y. Inoue Chem. Rev. 92 1992 741
3. (c) S.R.L. Everitt Y. Inoue V. Ramamurthy K.S. Shanze Molecular and Supramolecular Photochemistry Vol. 3 1999 Marcel Dekker New York 71
4. (d) J.-P. Pete Adv. Photochem. 21 1996 135
5. (a) D.M. White J. Am. Chem. Soc. 82 1960 5678
6. (b) H. Aoyama T. Hasegawa Y. Omote J. Am. Chem. Soc. 101 1979 5343
7. (c) R.A. Yellin B.S. Green J. Am. Chem. Soc. 102 1980 1157
8. (d) M. Vaida R. Popovitz-Biro L. Leiserowitz M. Lahav V. Ramamurthy Photochemistry in Organized and Constrained Media 1991 VCH New York 247
9. (e) A. Natarajan J.T. Mague V. Ramamurthy Cryst. Growth Des. 5 2005 2348
10. (f) J.N. Gamlin R. Jones M. Leibovitch B. Patrick J.R. Scheffer J. Trotter Acc. Chem. Res. 29 1996 203
11. (g) A. Natarajan J.T. Mague V. Ramamurthy J. Am. Chem. Soc. 127 2005 3568
12. (a) A. Joy V. Ramamurthy Chem. Eur. J. 6 2000 1287
13. (b) S. Koodanjeri A. Joy V. Ramamurthy Tetrahedron 56 2000 7003
14. (c) Y. Inoue T. Wada N. Sugahara K. Yamamoto K. Kimura L.-H. Tong X.-M. Gao Z.-J. Hou y. Liu J. Org. Chem. 65 2000 8041
15. (d) S. Koodanjeri J. Sivaguru A.R. Pradhan V. Ramamurthy Proc. Ind. Natl. Sci. Acad. 68 2002 453
16. (e) A. Joy L.S. Kaanumalle V. Ramamurthy Org. Biomol. Chem. 3 2005 3045
17. (f) N.J. Turro Acc. Chem. Res. 33 2000 637
18. (g) H. Saito J. Sivaguru S. Jockusch J. Dyer Y. Inoue W. Adam N.J. Turro Chem. Commun. 8 2007 819
19. (h) C.V. Kumar A. Buranaprapuk H.C. Sze S. Jockusch N.J. Turro Proc. Natl. Acad. Sci. U.S.A. 99 2002 5810
20. (a) A. Joy S. Uppili M.R. Netherton J.R. Scheffer V. Ramamurthy J. Am. Chem. Soc. 122 2000 728
21. (b) J. Sivaguru J.R. Scheffer V. Ramamurthy Chem. Commun. 2002 830
22. (c) N. Arunkumar K. Wang V. Ramamurthy J.R. Scheffer B. Patrick Org. Lett. 4 2002 1443
23. (d) N. Arunkumar A. Joy L.S. Kaanumalle J.R. Scheffer V. Ramamurthy J. Org. Chem. 67 2002 8339 8350
24. (e) J. Sivaguru J. Shailaja S. Uppili K. Ponchot A. Joy N. Arunkumar V. Ramamurthy F. Toda Organic Solid State Reactions 2002 Kluwer Academic Press Dordrecht, The Netherlands 159 188
25. (a) V. Ramamurthy A. Natarajan L.S. Kaanumalle S. Karthikeyan J. Sivaguru J. Shailaja A. Joy V. Ramamurthy Y. Inoue Chiral Photochemistry 2004 Marcel Dekker New York
26. (b) S. Karthikeyan L.S. Kaanumalle S. Uppili V. Ramamurthy Org. Biomol. Chem. 5 2007 1569
27. A. Joy J.R. Scheffer V. Ramamurthy Org. Lett. 2 2000 119
28. J. Sivaguru A. Natarajan L.S. Kaanumalle J. Shailaja S. Uppili A. Joy V. Ramamurthy Acc. Chem. Res. 36 2003 509
29. J. Sivaguru T. Poon R. Franz S. Jockusch W. Adam N.J. Turro J. Am. Chem. Soc. 126 2004 10816
30. (a) Weiqiang Gu Manoj Warrier V. Ramamurthy Richard G. Weiss J. Am. Chem. Soc. 121 1999 9467
31. (b) K. Pitchumani M. Warrier C. Cui R.G. Weiss V. Ramamurthy Tetrahedron Lett. 37 1996 6251
32. (c) N.J. Turro P. Wan J. Am. Chem. Soc. 107 1985 678
33. (d) M. Warrier L.S. Kaanumalle V. Ramamurthy Can. J. Chem. 81 2003 620
34. (e) V. Ramamurthy D.R. Corbin D.F. Eaton J. Org. Chem. 55 1990 5269
35. K. Pitchumani M. Warrier L.S. Kaanumalle V. Ramamurthy Tetrahedron 59 2003 5763
36. S. Arumugam L.S. Kaanumalle V. Ramamurthy Photochem. Photobiol. 82 2006 139
37. (a) G.S. Hammond R.S. Cole J. Am. Chem. Soc. 87 1965 3256 3257
38. (b) Y. Inoue N. Yamasaki H. Shimoyama A. Tai J. Org. Chem. 58 1993 1785
39. (a) H. Hart R.K. Murray J. Org. Chem. 35 1970 1535
40. (b) E. Cheung M.R. Netherton J.R. Scheffer J. Trotter Tetrahedron Lett. 40 1999 8737
41. (a) E.J. Corey J. Streith J. Am. Chem. Soc. 86 1964 950
42. (b) R.C. De Selms W.R. Schleigh Tetrahedron Lett. 34 1972 3563
43. (a) J. Sivaguru J.R. Scheffer J. Chandrasekhar V. Ramamurthy J. Chem. Soc., Chem. Commun. 2002 830
44. (b) S. Jayaraman S. Uppili A. Natarajan A. Joy K.C.W. Chong M.R. Netherton A. Zenova J.R. Scheffer V. Ramamurthy Tetrahedron Lett. 41 2000 8231
45. (a) R.A. Komoroski K.A. Mauritz J. Am. Chem. Soc. 100 1978 7487
46. (b) S.J. Sondheimer N.J. Bunce C.A. Fyfe J. Macromol. Sci. Rev. Macromol. Chem. Phys. C26 1986 353
47. (a) M.N. Szentirmay N.E. Prieto C.R. Martin J. Phys. Chem. 89 1985 3017
48. (b) E.-P. Niu K.P. Ghihhino T.A. Smith A.W.-H. Mau J. Lumin. 46 1990 191
49. (a) F. Ronald A.G. Mika J. Org. Chem. 47 1982 4204
50. (b) C.H. Tung J.G. Qu J. Org. Chem. 61 1996 9417
51. (c) C.H. Tung J.G. Qu J. Org. Chem. 63 1998 5857
52. (d) C.H. Tung J.Q. Guan J. Am. Chem. Soc. 120 1998 11874
53. (e) C.H. Tung X.H. Xu Tetrahedron Lett. 40 1999 127
54. (f) X.H. Li L.Z. Wu L.P. Zhang C.H. Tung Org. Lett. 4 2002 1175
55. (g) X.H. Li L.Z. Wu L.P. Zhang C.H. Tung Org. Lett. 4 2002 1175
56. (a) P.C. Lee D. Meisel Photochem. Photobiol. 41 1985 21
57. (b) E. Blatt A. Launikonis A.W.H. Mau W.H.F. Sasse Aust. J. Chem. 40 1987 1
58. (c) D. Weir J.C. Scaiano Tetrahedron 43 1987 1617
59. T.D. Gierke E. Munn F.C. Wilson J. Polym. Sci., Part B: Polym. Phys. 19 1981 1687
60. (a) J. Sivaguru R.B. Sunoj T. Wada Y. Origane Y. Inoue V. Ramamurthy J. Org. Chem. 69 2004 5528
61. (b) J. Sivaguru J. Shailaja S. Uppili K. Ponchot A. Joy N. Arunkumar V. Ramamurthy F. Toda Organic Solid State Reactions 2002 Kluwer Academic Press Dordrecht, The Netherlands 159 188