The mechanism of photoinduced acylation of amines by N-acyl-5,7- dinitroindoline as determined by time-resolved infrared spectroscopy

Organic Letters

Volumn 7, Issue 14, 2005, Pages 2845-2848

  Cohen, Andrew D ^a   Helgen, Céline ^b   Bochet, Christian G ^b   Toscano, John P ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 22244472988     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050670f     Document Type: Article

References (19)

1. (a) Bochet, C. G. J. Chem. Soc., Perkin Trans. 1 2002, 125-142.
2. (b) Pelliccioli, A. P.; Wirz, J. Photochem. Photobiol. Sci. 2002, 1, 441-458.
3. Amit, B.; Ben-Efraim, D. A.; Patchornik, A. J. Am. Chem. Soc. 1976, 98, 843-844.
4. Pass, S.; Amit, B.; Patchornik, A. J. Am. Chem. Soc. 1981, 103, 7674-7675.
5. Helgen, C.; Bochet, C. G. Synlett 2001, 1968-1970.
6. Nicolaou, K. C.; Safina, B. S.; Winssinger, N. Synlett 2001, 900-903.
7. (a)Vizvardi, K.; Kreutz, C.; Davis, A. S.; Lee, V. P.; Philmus, B. J.; Simo, O.; Michael, K. Chem. Lett. 2003, 32, 348-349.
8. (b) Simo, O.; Lee, V. P.; Davis, A. S.; Kreutz, C.; Gross, P. H.; Jones, P. R.; Michael, K. Carbohydr. Res. 2005, 340, 557-566.
9. Helgen, C.; Bochet, C. G. J. Org. Chem. 2003, 68, 2483-2486.
10. (a) Canepari, M.; Papageorgiou, G.; Corrie, J. E. T.; Watkins, C.; Ogden, D. J. Physiol. 2001, 533, 765-772.
11. (b) Canepari, M.; Nelson, L.; Papageorgiou, G.; Corrie, J. E. T.; Ogden, D. J. Neurosci. Methods 2001, 112, 29-42.
12. (c) Lowe, G. J. Neurophysiol. 2003, 90, 1737-1746.
13. Morrison, J.; Wan, P.; Corrie, J. E. T.; Papageorgiou, G. Photochem. Photobiol. Sci. 2002, 1, 960-969.
14. (a) Corrie, J. E. T.; Barth, A.; Munasinghe, V. R. N.; Trentham, D. R.; Hutter, M. C. J. Am. Chem. Soc. 2003, 125, 8546-8554.
15. (b) Il'ichev, Y. V.; Schworer, M. A.; Wirz, J. J. Am. Chem. Soc. 2004, 126, 4581.
16. Mortensen, M. B.; Kamounah, F. S.; Christensen, J. B. Org. Prep. Proc. Int. 1996, 28, 123-125.
17. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
18. We also examined the photochemistry of 1 by laser flash photolysis (LFP) using UV detection. By LFP, syn-7 and anti-7 are indistinguishable, so the transient absorption band was symmetric. Additionally, the derived second-order rate constant was the same in both the LFP and TRIR experiments (Supporting Information).
19. 7