Photochemical carbon skeletal rearrangement of cyclic Baylis-Hillman products: Ring contraction or not? That is the question

Synlett

Volumn , Issue 4, 2000, Pages 491-492

  Mikami, Koichi ^a   Okubo, Yasutaka ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

1,4 diketone; Cyclic Baylis Hillman product; Photochemical rearrangement; Ring contraction

Indexed keywords

KETONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; PHOTOCHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034087506     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (19)

1. Mattay, J.; Griesbeck, A. G. Photochemical Key Steps in Organic Synthesis; VCH: New York, 1994. Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific: Oxford, 1991. Porco, J. A. Jr.; Schreiber, S. L. Comprehensive Organic Synthesis; Pergamon: London, 1991; Vol. 5, p. 151. Wagner, P. J. Rearrangement in Ground and Excited States, de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 3, p. 384. Koizumi, M.; Kato, S.; Mataga, N.; Matsuura, T.; Usui, Y. Photosensitized Reactions; Kagakudojin: Kyoto, 1978. Ramamurthy, V.; Turro, N. J., Eds. Chem. Rev. 1993, 93, 1. Yoon, U. C.; Mariano P. S. Acc. Chem. Res. 1992, 25, 233. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227. Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
2. Mattay, J.; Griesbeck, A. G. Photochemical Key Steps in Organic Synthesis; VCH: New York, 1994. Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific: Oxford, 1991. Porco, J. A. Jr.; Schreiber, S. L. Comprehensive Organic Synthesis; Pergamon: London, 1991; Vol. 5, p. 151. Wagner, P. J. Rearrangement in Ground and Excited States, de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 3, p. 384. Koizumi, M.; Kato, S.; Mataga, N.; Matsuura, T.; Usui, Y. Photosensitized Reactions; Kagakudojin: Kyoto, 1978. Ramamurthy, V.; Turro, N. J., Eds. Chem. Rev. 1993, 93, 1. Yoon, U. C.; Mariano P. S. Acc. Chem. Res. 1992, 25, 233. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227. Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
3. Mattay, J.; Griesbeck, A. G. Photochemical Key Steps in Organic Synthesis; VCH: New York, 1994. Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific: Oxford, 1991. Porco, J. A. Jr.; Schreiber, S. L. Comprehensive Organic Synthesis; Pergamon: London, 1991; Vol. 5, p. 151. Wagner, P. J. Rearrangement in Ground and Excited States, de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 3, p. 384. Koizumi, M.; Kato, S.; Mataga, N.; Matsuura, T.; Usui, Y. Photosensitized Reactions; Kagakudojin: Kyoto, 1978. Ramamurthy, V.; Turro, N. J., Eds. Chem. Rev. 1993, 93, 1. Yoon, U. C.; Mariano P. S. Acc. Chem. Res. 1992, 25, 233. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227. Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
4. Mattay, J.; Griesbeck, A. G. Photochemical Key Steps in Organic Synthesis; VCH: New York, 1994. Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific: Oxford, 1991. Porco, J. A. Jr.; Schreiber, S. L. Comprehensive Organic Synthesis; Pergamon: London, 1991; Vol. 5, p. 151. Wagner, P. J. Rearrangement in Ground and Excited States, de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 3, p. 384. Koizumi, M.; Kato, S.; Mataga, N.; Matsuura, T.; Usui, Y. Photosensitized Reactions; Kagakudojin: Kyoto, 1978. Ramamurthy, V.; Turro, N. J., Eds. Chem. Rev. 1993, 93, 1. Yoon, U. C.; Mariano P. S. Acc. Chem. Res. 1992, 25, 233. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227. Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
5. Mattay, J.; Griesbeck, A. G. Photochemical Key Steps in Organic Synthesis; VCH: New York, 1994. Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific: Oxford, 1991. Porco, J. A. Jr.; Schreiber, S. L. Comprehensive Organic Synthesis; Pergamon: London, 1991; Vol. 5, p. 151. Wagner, P. J. Rearrangement in Ground and Excited States, de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 3, p. 384. Koizumi, M.; Kato, S.; Mataga, N.; Matsuura, T.; Usui, Y. Photosensitized Reactions; Kagakudojin: Kyoto, 1978. Ramamurthy, V.; Turro, N. J., Eds. Chem. Rev. 1993, 93, 1. Yoon, U. C.; Mariano P. S. Acc. Chem. Res. 1992, 25, 233. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227. Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
6. Mattay, J.; Griesbeck, A. G. Photochemical Key Steps in Organic Synthesis; VCH: New York, 1994. Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific: Oxford, 1991. Porco, J. A. Jr.; Schreiber, S. L. Comprehensive Organic Synthesis; Pergamon: London, 1991; Vol. 5, p. 151. Wagner, P. J. Rearrangement in Ground and Excited States, de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 3, p. 384. Koizumi, M.; Kato, S.; Mataga, N.; Matsuura, T.; Usui, Y. Photosensitized Reactions; Kagakudojin: Kyoto, 1978. Ramamurthy, V.; Turro, N. J., Eds. Chem. Rev. 1993, 93, 1. Yoon, U. C.; Mariano P. S. Acc. Chem. Res. 1992, 25, 233. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227. Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
7. Mattay, J.; Griesbeck, A. G. Photochemical Key Steps in Organic Synthesis; VCH: New York, 1994. Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific: Oxford, 1991. Porco, J. A. Jr.; Schreiber, S. L. Comprehensive Organic Synthesis; Pergamon: London, 1991; Vol. 5, p. 151. Wagner, P. J. Rearrangement in Ground and Excited States, de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 3, p. 384. Koizumi, M.; Kato, S.; Mataga, N.; Matsuura, T.; Usui, Y. Photosensitized Reactions; Kagakudojin: Kyoto, 1978. Ramamurthy, V.; Turro, N. J., Eds. Chem. Rev. 1993, 93, 1. Yoon, U. C.; Mariano P. S. Acc. Chem. Res. 1992, 25, 233. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227. Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
8. Mattay, J.; Griesbeck, A. G. Photochemical Key Steps in Organic Synthesis; VCH: New York, 1994. Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific: Oxford, 1991. Porco, J. A. Jr.; Schreiber, S. L. Comprehensive Organic Synthesis; Pergamon: London, 1991; Vol. 5, p. 151. Wagner, P. J. Rearrangement in Ground and Excited States, de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 3, p. 384. Koizumi, M.; Kato, S.; Mataga, N.; Matsuura, T.; Usui, Y. Photosensitized Reactions; Kagakudojin: Kyoto, 1978. Ramamurthy, V.; Turro, N. J., Eds. Chem. Rev. 1993, 93, 1. Yoon, U. C.; Mariano P. S. Acc. Chem. Res. 1992, 25, 233. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227. Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
9. Mattay, J.; Griesbeck, A. G. Photochemical Key Steps in Organic Synthesis; VCH: New York, 1994. Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell Scientific: Oxford, 1991. Porco, J. A. Jr.; Schreiber, S. L. Comprehensive Organic Synthesis; Pergamon: London, 1991; Vol. 5, p. 151. Wagner, P. J. Rearrangement in Ground and Excited States, de Mayo, P. Ed.; Academic Press: New York, 1980, Vol. 3, p. 384. Koizumi, M.; Kato, S.; Mataga, N.; Matsuura, T.; Usui, Y. Photosensitized Reactions; Kagakudojin: Kyoto, 1978. Ramamurthy, V.; Turro, N. J., Eds. Chem. Rev. 1993, 93, 1. Yoon, U. C.; Mariano P. S. Acc. Chem. Res. 1992, 25, 233. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227. Crimmins, M. T. Chem. Rev. 1988, 88, 1453.
10. Matsumoto, S., Okubo, Y., Mikami, K. J. Am. Chem. Soc. 1998, 129, 4015.
11. Trost, B. M. Chem. Soc. Rev. 1982, 11, 41. Texier-Boullet, F.; Klein, B.; Hamelin, J. Synthesis 1986, 409.
12. Trost, B. M. Chem. Soc. Rev. 1982, 11, 41. Texier-Boullet, F.; Klein, B.; Hamelin, J. Synthesis 1986, 409.
13. Excellent textbook on ring contraction: Fuhrhop, J.; Penzlin, G. Organic Synthesis, Concepts, Methods, Starting Materials Verlag: Weinheim, 1983.
14. The photoreaction in ether solution gave products in the highest yield in these cases.
15. Excellent textbook on carbocyclic chemistry: Mundy, B. P. Concepts of Organic Synthesis: Carbocyclic Chemistry Marcel Dekker: New York, 1979.
16. Bailey, M.; Staton, I.; Ashton, P. R.; Markó, I. E.; Ollis, W. D. Tetrahedron: Asymmetry 1991, 2, 495.
17. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227. Scaiano, J. C.; Lissi, E. A.; Encina, M. V. Rev. Chem. Intermediates 1978, 2, 139. Baum, E. J.; Wan, J. K. S.; Pitts, J. N. Jr. J. Am. Chem. Soc. 1966, 88, 2652.
18. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227. Scaiano, J. C.; Lissi, E. A.; Encina, M. V. Rev. Chem. Intermediates 1978, 2, 139. Baum, E. J.; Wan, J. K. S.; Pitts, J. N. Jr. J. Am. Chem. Soc. 1966, 88, 2652.
19. Wagner, P. J.; Park, B. -S. Org. Photochem. 1991, 11, 227. Scaiano, J. C.; Lissi, E. A.; Encina, M. V. Rev. Chem. Intermediates 1978, 2, 139. Baum, E. J.; Wan, J. K. S.; Pitts, J. N. Jr. J. Am. Chem. Soc. 1966, 88, 2652.