Self-Sensitized Photooxygenation of 2H-Pyrans: Characterization of Unexpected Products Assisted by Computed Structural Elucidation and Residual Dipolar Couplings

Journal of Organic Chemistry

Volumn 80, Issue 15, 2015, Pages 7396-7402

  Riveira, Martín J ^a   Trigo Mouriño, Pablo ^b   Troche Pesqueira, Eduardo ^b,c   Martin, Gary E ^d   Navarro Vázquez, Armando ^e   Mischne, Mirta P ^a   Gil, Roberto R ^b  

^a Universidad Nacional de Rosario   (Argentina)

^b CARNEGIE MELLON UNIVERSITY   (United States)

^c UNIVERSITY OF VIGO   (Spain)

^d MERCK RESEARCH LABORATORIES   (United States)

^e FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

IRRADIATION;

BETA POSITION; COMPUTER ASSISTED; DOUBLE-QUANTUM; PHOTOOXYGENATIONS; RESIDUAL DIPOLAR COUPLINGS; STRUCTURAL ELUCIDATION; STRUCTURAL POSSIBILITIES; STRUCTURE ELUCIDATION;

COUPLINGS;

EPOXIDE; OXETANE DERIVATIVE; PYRAN DERIVATIVE; SINGLET OXYGEN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COMPUTER PROGRAM; CROSS COUPLING REACTION; CYCLOADDITION; PHOTOCHEMISTRY; PHOTOOXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; STEREOCHEMISTRY; ULTRAVIOLET A RADIATION; ULTRAVIOLET IRRADIATION;

EID: 84938818169     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00817     Document Type: Article

References (51)

1. Montagnon, T.; Tofi, M.; Vassilikogiannakis, G. Acc. Chem. Res. 2008, 41, 1001-1011
2. Buchanan, G. S.; Cole, K. P.; Tang, Y.; Hsung, R. P. J. Org. Chem. 2011, 76, 7027-7039
3. Peng, W.; Hirabaru, T.; Kawafuchi, H.; Inokuchi, T. Eur. J. Org. Chem. 2011, 2011, 5469-5474
4. Kepler, J. A.; Philip, A.; Lee, Y. W.; Morey, M. C.; Carroll, F. I. J. Med. Chem. 2002, 31, 713-716
5. Etoh, H.; Ina, K.; Iguichi, M. Agric. Biol. Chem. 1973, 37, 2241-2244
6. Huber, S.; Mischne, M. Nat. Prod. Res. 1995, 7, 43-46
7. Mischne, M. P.; Huber, S. N.; Zinczuk, J. Can. J. Chem. 1999, 77, 237-242
8. Borsarelli, C. D.; Mischne, M.; La Venia, A.; Moran Vieyra, F. E. Photochem. Photobiol. 2007, 83, 1313-1318
9. Coelho, P. J.; Carvalho, L. M.; Vermeersch, G.; Delbaere, S. Tetrahedron 2009, 65, 5369-5376
10. Huang, C.-N.; Kuo, P.-Y.; Lin, C.-H.; Yang, D.-Y. Tetrahedron 2007, 63, 10025-10033
11. Riveira, M. J.; Mischne, M. P. Synth. Commun. 2013, 43, 208-220
12. Bax, A.; Freeman, R.; Frenkiel, T. A. J. Am. Chem. Soc. 1981, 103, 2102-2104
13. Weigelt, J.; Otting, G. J. Magn. Reson., Ser. A 1995, 113, 128-130
14. Reif, B.; Köck, M.; Kerssebaum, R.; Kang, H.; Fenical, W.; Griesinger, C. J. Magn. Reson., Ser. A 1996, 118, 282-285
15. Reif, B.; Köck, M.; Kerssebaum, R.; Schleucher, J.; Griesinger, C. J. Magn. Reson., Ser. A 1996, 112, 295-301
16. Martin, G. E. Annu. Rep. NMR Spectrosc. 2011, 74, 215-291
17. Martin, G. E.; Reibarkh, M.; Buevich, A. V.; Blinov, K. A.; Williamson, R. T. eMagRes 2014, 3, 215-234
18. Blinov, K. A.; Larin, N. I.; Williams, A. J.; Mills, K. A.; Martin, G. E. J. Heterocycl. Chem. 2006, 43, 163-166
19. Snyder, D. A.; Brüschweiler, R. J. Phys. Chem. A 2009, 113, 12898-12903
20. ACD/Structure Elucidator Suite-Elucidate Unknown Structures. http://www.acdlabs.com/products/com-iden/elucidation/struc-eluc (accessed Feb 12, 2015).
21. Rychnovsky, S. D. Org. Lett. 2006, 13, 2895-2898
22. Kummerlöwe, G.; Crone, B.; Kretschmer, M.; Kirsch, S. F.; Luy, B. Angew. Chem., Int. Ed. 2011, 50, 2643-2645
23. Gil, R. R.; Gayathri, C.; Tsarevsky, N. V.; Matyjaszewski, K. J. Org. Chem. 2008, 73, 840-848
24. Trigo-Mouriño, P.; Navarro-Vázquez, A.; Ying, J.; Gil, R. R.; Bax, A. Angew. Chem., Int. Ed. 2011, 50, 7576-7580
25. Thiele, C. M. Concepts Magn. Reson., A 2007, 30A, 65-80
26. Gayathri, C.; Tsarevsky, N. V.; Gil, R. R. Chem.-Eur. J. 2010, 16, 3622-3626
27. Freudenberger, J. C.; Spiteller, P.; Bauer, R.; Kessler, H.; Luy, B. J. Am. Chem. Soc. 2004, 126, 14690-14691
28. Aroulanda, C.; Sarfati, M.; Courtieu, J.; Lesot, P. Enantiomer 2001, 6, 281-287
29. Thiele, C. M.; Bermel, W. J. Magn. Reson. 2012, 216, 134-143
30. Furrer, J.; John, M.; Kessler, H.; Luy, B. J. Biomol. NMR 2007, 37, 231-243
31. Losonczi, J. A.; Andrec, M.; Fischer, M. W.; Prestegard, J. H. J. Magn. Reson. 1999, 138, 334-342
32. Navarro-Vázquez, A. Magn. Reson. Chem. 2012, 50, S73-S79
33. Thiele, C. M.; Schmidts, V.; Böttcher, B.; Louzao, I.; Berger, R.; Maliniak, A.; Stevensson, B. Angew. Chem., Int. Ed. 2009, 48, 6708-6712
34. Cornilescu, G.; Bax, A. J. Am. Chem. Soc. 2000, 122, 10143-10154
35. Smith, S. G.; Goodman, J. M. J. Am. Chem. Soc. 2010, 132, 12946-12959
36. Riveira, M. J.; Gayathri, C.; Navarro-Vázquez, A.; Tsarevsky, N. V.; Gil, R. R.; Mischne, M. P. Org. Biomol. Chem. 2011, 9, 3170-3175
37. Trigo-Mouriño, P.; Sifuentes, R.; Navarro-Vázquez, A.; Gayathri, C.; Maruenda, H.; Gil, R. R. Nat. Prod. Commun. 2012, 7, 735-738
38. Maheshwari, K. K.; de Mayo, P.; Wiegand, D. Can. J. Chem. 1970, 48, 3265-3268
39. Jeger, O.; Schaffner, K.; Wehrli, H. Pure Appl. Chem. 1964, 9, 555-566
40. Williams, J. R.; Sarkisian, G. M.; Quigley, J.; Hasiuk, A.; VanderVennen, R. J. Org. Chem. 1974, 39, 1028-1032
41. Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104-6155
42. Zheng, Y.; Tice, C. M.; Singh, S. B. Bioorg. Med. Chem. Lett. 2014, 24, 3673-3682
43. Valenta, P.; Drucker, N. A.; Bode, J. W.; Walsh, P. J. Org. Lett. 2009, 11, 2117-2119
44. Halgren, T. A. J. Comput. Chem. 1996, 17, 490-519
45. Halgren, T. A.; Nachbar, R. B. J. Comput. Chem. 1996, 17, 587-615
46. Schrödinger Release 2014-1: MacroModel, version 10.3; Schrödinger, LLC: New York, 2014.
47. Frisch, M. J., Gaussian09, revision D.01; Gaussian Inc.: Wallingford, CT, 2009.
48. Zhang, Y.; Wu, A.; Xu, X.; Yan, Y. Chem. Phys. Lett. 2006, 421, 383-388
49. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
50. Paier, J.; Hirschl, R.; Marsman, M.; Kresse, G. J. Chem. Phys. 2005, 122, 234102
51. Jensen, F. J. Chem. Theory Comput. 2008, 4, 719-727