Complete memory of chirality upon photodecarboxylation of mesityl alkanoate to mesitylalkane: Theoretical and experimental evidence for cheletropic decarboxylation via a spiro-lactonic transition state

Chemical Communications

Volumn 3, Issue 18, 2003, Pages 2302-2303

  Mori, Tadashi ^a   Saito, Hideaki ^a   Inoue, Yoshihisa ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; ALKANOIC ACID; SPIRONOLACTONE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DECARBOXYLATION; ENANTIOMER; ENERGY TRANSFER; STEREOCHEMISTRY; THEORETICAL STUDY;

EID: 0141455987     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b305267b     Document Type: Article

References (36)

1. J. A. Pincock, in CRC Handbook of Organic Photochemistry, ed. W. M. Horspool and P.-S. Song, CRC Press, Boca Raton, FL, 1995, p. 393
2. E. Rusu, E. Comanita, M. Onciu, Quart. Rev. 2000, 7, 241
3. R. Martin, Org. Prep. Proc. Int. 1992, 24, 369
4. D. Bellus, Adv. Photochem. 1971, 8, 109
5. D. Budac, P. Wan, J. Photochem. Photobiol. A, 1992, 67, 135
6. R. A. Finnegan, D. Knutson, Chem. Commun. 1966, 172
7. H. J. Hageman, Tetrahedron, 1969, 25, 6015
8. J. S. Bradshaw, E. L. Loveridge, L. White, J. Org. Chem. 1968, 33, 4127
9. T. Mori, T. Wada, Y. Inoue, Org. Lett. 2000, 2, 3401
10. R. A. Finnegan, D. Knutson, Tetrahedron Lett. 1968, 3429
11. H. J. Hageman, Tetrahedron, 1969, 25, 6015
12. R. A. Finnegan, D. Knutson, J. Am. Chem. Soc. 1967, 89, 1970
13. W. Bhanthumnavin, W. G. Bentrude, J. Org. Chem. 2001, 66, 980
14. F. Gao, D. Boyles, R. Sullivan, R. N. Compton, R. M. Pagni, J. Org. Chem. 2002, 67, 9361
15. L. Verbit, A. S. Rao, J. W. Clark-Lewis, Tetrahedron, 1968, 24, 5839
16. L. Verbit, J. Am. Chem. Soc. 1965, 87, 1617
17. L. J. Mittal, J. P. Mittal, E. Hayon, J. Phys. Chem. 1973, 77, 1482
18. K.-W. Lee, N. Horowitz, J. Ware, L. A. Singer, J. Am. Chem. Soc. 1977, 99, 2622
19. A. G. Griesbeck, W. Kramer, J. Lex, Angew. Chem. Int. Ed. 2001, 40, 577
20. B. Giese, P. Wettstein, C. Stähelin, F. Barbosa, M. Neuburger, M. Zehnder, P. Wessig, Angew. Chem. Int. Ed. 1999, 38, 2586
21. F. D. Lewis, J. G. Magyar, J. Am. Chem. Soc. 1973, 95, 5973
22. F. Monnat, P. Vogel, V. M. Rayon, J. A. Sordo, J. Org. Chem. 2002, 67, 1882
23. E. Roversi, F. Monnat, P. Vogel, K. Schenk, P. Roversi, Helv. Chim. Acta, 2002, 85, 733
24. F. Monnat, P. Vogel, J. A. Sordo, Helv. Chim. Acta, 2002, 85, 712
25. H. Kessler, A. Rieker, Justus Liebigs Ann. Chem. 1967, 708, 57
26. H. Kessler, A. Rieker, Z. Naturforsch. B, 1967, 22, 456
27. M. Oki, H. Nakanishi, Bull. Chem. Soc. Jpn. 1971, 44, 3148
28. K. Sakamoto, M. Oki, Bull. Chem. Soc. Jpn. 1974, 47, 2623
29. H. Nakanishi, H. Fujita, O. Yamamoto, Bull. Chem. Soc. Jpn. 1978, 51, 214
30. A. G. Merzlikine, S. V. Voskresensky, E. O. Danilov, M. A. J. Rodgers, D. C. Neckers, J. Am. Chem. Soc. 2002, 124, 14532
31. P. Hohenberg, W. Kohn, Phys. Rev. B, 1964, 136, 864
32. W. Kohn, L. J. Sham, Phys. Rev. A, 1965, 140, 1133
33. R. G. Parr and W. Wang, Density functional theory of atoms and molecules, Oxford University Press, Oxford, 1989
34. W. Gu, D. J. Abdallah, R. G. Weiss, J. Photochem. Photobiol. A, 2001, 139, 79
35. A. K. Singh, S. M. Sonar, Synth. Commun. 1985, 15, 1113
36. A. Lalitha, K. Pitchumani, C. Srinivasan, Tetrahedron, 2001, 57, 4455