DOI QR코드

DOI QR Code

Azomethine Yilde Forming Photoreaction of N-(Tributylstannyl)methylphthalimide

N-(트리부틸스탄일)메틸프탈이미드의 아조메틴 일리드 형성 광화학 반응

  • Published : 2009.06.20

Abstract

Investigation was conducted to examine whether photochemical reaction of N-(tributylstannyl)- methylphthalimide generates an azomethine ylide intermediate in its excited state as its silyl derivative N-(trimethylsilyl)methylphthalimide which has been observed to form an azomethine ylide. The irradiation of N-(tributylstannyl)methylphthalimide in $D_2O-CH_3$CN generates mono-deuterated N-methylphthalimide as an exclusive product which supports the efficient generation of azomethine ylide intermediate and its trapping by water molecule through a proto-destannylation pathway. However the generated tributylstannyl subsitiuted ylide was not observed to be trapped with a dipolarophile such as methyl acrylate and acrylonitrile present in the reactions which is in contrast with the ylide from N-(trimethylsilyl)methylphthalimide.

Keywords

N-(tributylstaanyl)methylphthalimide;Azomethine ylide;Photochemical reaction;Mono-deuterated N-methylphthalimide

References

  1. Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407 https://doi.org/10.1021/ar50131a002
  2. Colye, J. D. In Synthetic Organic Photochemistry Horspool, W. M. Ed.; Plenum Press: New York, U. S. A., 1984; p 259
  3. Mazzocchi, P. H. In Organic Photochemistry Padwa, A. Ed.; Marcel Dekker: New York, U. S. A., 1981; Vol. 5, p 421
  4. Yoon, U. C.; Mariano, P. S. In Organic Photochemistry and Photophysics Ramamurthy, V.; Schanze, K. Ed.; CRC Press,Talyor & Francis, Boca Raton, FL. U. S. A., 2006; p 179
  5. Yoon, U. C.; Mariano, P. S. In CRC Handbook of Organic Photochemistry and Photobiology 2nd Edition Ramamurthy, V.; Schanze, K. Ed.; CRC Press, Talyor &Boca Raton, FL. U. S. A.,2003; Vol. 85,p 1
  6. Yoon, U. C. Mariano, P. S. Acc. Chem. Res. 2001, 34(7), 523 https://doi.org/10.1021/ar010004o
  7. Yoon, U. C. Jin, Y. X.; Oh, S.W.; Cho, D. W.; Park, K. H.; Mariano, P. S. J. Photochem. Photobiol. A :. 2002, 150, 77 https://doi.org/10.1016/S1010-6030(02)00032-1
  8. Yoon, U. C Oh, S. W.; Lee, J. H.; Park, J. H.; Kang, K. T.; Mariano, P. S., J. Org. Chem. 2001, 66(3), 939 https://doi.org/10.1021/jo001457u
  9. Yoon, U. C.; Jin, Y. X.; Oh, S. W.; Park, C. H.; Park, J. H.; Campana, C. F. Cai, X.; Duesler, E. N. Mariano, P. S. J. Am. Chem. Soc. 2003, 125(35), 10664 https://doi.org/10.1021/ja030297b
  10. Yoon, U. C.; Kwon, H. C.; Hyung, T. G.; Choi, K. H.; Oh, S. W.;Yang, S.; Zhao, Z.; Mariano, P. S. J. Am. Chem. Soc. 2004, 126(4), 1110 https://doi.org/10.1021/ja0305712
  11. Cho, D. W. Choi, J. H. Oh, S. W. Quan, C. Yoon, U. C. Wang, R. Yang, S. Mariano, P. S. J. Am. Chem. Soc. 2008, 130(7), 2276 https://doi.org/10.1021/ja076846l
  12. Yoon, U. C. Oh, S. W. Lee, C. W. Heterocycles 1995, 41(12), 2665 https://doi.org/10.3987/COM-95-7029
  13. Wang, R. Zhao, Z. Mariano, P. S.; Choi, K. H. Kim, S. H. Yoon, U. C. J. Photochem. Photobiol. A: Chem. 2005, 175(2-3), 232 https://doi.org/10.1016/j.jphotochem.2005.05.005
  14. Yoon, U. C.; Jin, Y. X.; Oh, S.W.; Cho, D. W.; Park, K. H.; Mariano, P. S. J. Photochem. Photobiol. A :. 2002, 150, 77 https://doi.org/10.1016/S1010-6030(02)00032-1
  15. Maeda, H.; Tierney, D. L. Mariano, P. S. Banerjee, M.; Cho, D. W.; Yoon, U. C. Tetrahedron 2008, 64(22), 5268 https://doi.org/10.1016/j.tet.2008.03.031
  16. Yoon,U. C. Kim, D. U. Kim, J. C. Lee, J. G. Mariano, P. S. Lee, Y. J. and Ammon, H. L. Tetrahedron Lett. 1993, 34, 5859 https://doi.org/10.1016/S0040-4039(00)73798-1
  17. Yoon,U. C. Kim, D. U. Lee, C. W. Choi, Y. S. Lee, Y. J. Ammon, H. L. Mariano, P. S. J. Am. Chem. Soc. 1995, 117, 2698 https://doi.org/10.1021/ja00115a004
  18. Yoon, U. C. Cho, S. J. Lee, Y. J. Mancheno, M. J. Mariano, P. S. J. Org. Chem. 1995, 60(8), 2353 https://doi.org/10.1021/jo00113a012
  19. Lee, Y. J.; Lee, C. P. Jeon, Y. T. Mariano, P. S. Yoon, U. C. Tetrahedron Lett. 1993, 34, 5855 https://doi.org/10.1016/S0040-4039(00)73797-X
  20. Lee, Y. J. Ling, R. Mariano, P. S. Yoon, U. C. Kim, D. U. Oh, S. W., J. Org. Chem. 1996, 61(10), 3304-3314 https://doi.org/10.1021/jo9522623
  21. Yoon, U. C. Oh, S. W. Lee, S. M. Cho, S. J. Gamlin, J. Mariano, P. S., J. Org. Chem. 1999, 64(12), 4411-4418 https://doi.org/10.1021/jo990087a
  22. Yoon, U. C. Oh, S. W. Mancheno, M. Su, Z. Falvey, D. F. Mariano, P. S., J. Am. Chem. Soc. 1999, 121 (16), 3926-3932 https://doi.org/10.1021/ja9841862
  23. Davis, D. D.; Chambers, R. L.; Johnson, H. T., J. Organomet. Chem. 1970, 25, C13 https://doi.org/10.1016/S0022-328X(00)86187-2