(Z)-1-Aryl-1-haloalkenes as Intermediates in the Vilsmeier Haloformylation of Aryl Ketones

Organic Letters

Volumn 5, Issue 19, 2003, Pages 3387-3390

  Lilienkampf, Annamaria ^a   Johansson, Mikael P ^a   Wähälä, Kristiina ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ENAMINOKETONE; KETONE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ELECTRON; SUBSTITUTION REACTION; VILSMEIER HAACK REACTION;

EID: 0344741442     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034914c     Document Type: Article

References (46)

1. Vilsmeier, A.; Haack, A. Chem. Ber. 1927, 60, 119.
2. (a) Arnold, Z.; Zemlicka, J. Proc. Chem. Soc. 1958, 227.
3. For reviews, see: (b) Marson, C. M. Tetrahedron 1992, 48, 3659-3726. (c) Marson, C. M.; Giles, P. M. Synthesis Using Vilsmeier Reagents; CRC Press: Boca Raton, FL, 1994; pp 83-108. (d) Jones, G.; Stanworth, S. P. In Organic Reactions; Overman, L. E., Bittman, R., Ciganek, E., Curran, D., Denmark, S. E., Hegedus, L., Joyce, R. M., Martinelli, M. J., McCombie, S. W., Press, J. B., Press, L. S., Rajanbabu, T. V., Rigby, J. H., Roush, W. R., Smith, A. B., Wipf, P., Eds.; John Wiley & Sons, Inc.: New York, 2000; Vol. 56, Chapter 2, 373-384. (e) Juzt, C. Advances in Organic Chemistry. In Iminiumsalts in Organic Chemistry; Taylor, E. C., Ed.; John Wiley: New York, 1976; Vol. 9, Part 1, pp 225-342.
4. For reviews, see: (b) Marson, C. M. Tetrahedron 1992, 48, 3659-3726. (c) Marson, C. M.; Giles, P. M. Synthesis Using Vilsmeier Reagents; CRC Press: Boca Raton, FL, 1994; pp 83-108. (d) Jones, G.; Stanworth, S. P. In Organic Reactions; Overman, L. E., Bittman, R., Ciganek, E., Curran, D., Denmark, S. E., Hegedus, L., Joyce, R. M., Martinelli, M. J., McCombie, S. W., Press, J. B., Press, L. S., Rajanbabu, T. V., Rigby, J. H., Roush, W. R., Smith, A. B., Wipf, P., Eds.; John Wiley & Sons, Inc.: New York, 2000; Vol. 56, Chapter 2, 373-384. (e) Juzt, C. Advances in Organic Chemistry. In Iminiumsalts in Organic Chemistry; Taylor, E. C., Ed.; John Wiley: New York, 1976; Vol. 9, Part 1, pp 225-342.
5. For reviews, see: (b) Marson, C. M. Tetrahedron 1992, 48, 3659-3726. (c) Marson, C. M.; Giles, P. M. Synthesis Using Vilsmeier Reagents; CRC Press: Boca Raton, FL, 1994; pp 83-108. (d) Jones, G.; Stanworth, S. P. In Organic Reactions; Overman, L. E., Bittman, R., Ciganek, E., Curran, D., Denmark, S. E., Hegedus, L., Joyce, R. M., Martinelli, M. J., McCombie, S. W., Press, J. B., Press, L. S., Rajanbabu, T. V., Rigby, J. H., Roush, W. R., Smith, A. B., Wipf, P., Eds.; John Wiley & Sons, Inc.: New York, 2000; Vol. 56, Chapter 2, 373-384. (e) Juzt, C. Advances in Organic Chemistry. In Iminiumsalts in Organic Chemistry; Taylor, E. C., Ed.; John Wiley: New York, 1976; Vol. 9, Part 1, pp 225-342.
6. For reviews, see: (b) Marson, C. M. Tetrahedron 1992, 48, 3659-3726. (c) Marson, C. M.; Giles, P. M. Synthesis Using Vilsmeier Reagents; CRC Press: Boca Raton, FL, 1994; pp 83-108. (d) Jones, G.; Stanworth, S. P. In Organic Reactions; Overman, L. E., Bittman, R., Ciganek, E., Curran, D., Denmark, S. E., Hegedus, L., Joyce, R. M., Martinelli, M. J., McCombie, S. W., Press, J. B., Press, L. S., Rajanbabu, T. V., Rigby, J. H., Roush, W. R., Smith, A. B., Wipf, P., Eds.; John Wiley & Sons, Inc.: New York, 2000; Vol. 56, Chapter 2, 373-384. (e) Juzt, C. Advances in Organic Chemistry. In Iminiumsalts in Organic Chemistry; Taylor, E. C., Ed.; John Wiley: New York, 1976; Vol. 9, Part 1, pp 225-342.
7. (a) Mironov, A. F.; Kozhich, D. T.; Vasilevsky, V. I.; Evstigneeva, R. P. Synthesis 1979, 533-535.
8. (b) Prim, D.; Joseph, D.; Kirsch, G. Liebigs Ann. 1996, 239-245.
9. (c) Pulst, M.; Weißenfels, M.; Dietz, F. Z. Naturforsch 1985, 40b, 585-589.
10. (d) Brown, P. E.; Marcus, W. Y.; Anastasis, P. J. Chem. Soc., Perkin Trans. 1 1985, 1127-1136.
11. (e) Sciaky, R.; Pallini, U. Gazz. Chim. Ital. 1966, 96, 1241-1253.
12. (f) Marson, C. M.; Giles, P. M. Synthesis Using Vilsmeier Reagents; CRC Press: Boca Raton, FL, 1994; pp 41-42.
13. (4) However, Comins et al. have recognized that 4-chloro-1,2-dihydro- pyridines, which are cyclic chloroalkenes, were intermediates in the chloroformylation reaction of 2,3-dihydro-4-pyridones. See: (a) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. Tetrahedron Lett. 1992, 33, 7635-7638. (b) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. J. Org. Chem. 1993, 58, 7732-7739.
14. However, Comins et al. have recognized that 4-chloro-1,2-dihydro- pyridines, which are cyclic chloroalkenes, were intermediates in the chloroformylation reaction of 2,3-dihydro-4-pyridones. See: (a) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. Tetrahedron Lett. 1992, 33, 7635-7638. (b) Al-awar, R. S.; Joseph, S. P.; Comins, D. L. J. Org. Chem. 1993, 58, 7732-7739.
15. 4; after filtration, the solvent was evaporated.
16. (a) Bodendorf, K.; Mayer, R. Chem. Ber. 1965, 98, 3554-3560.
17. (b) Cox, M. T.; Holohan, J. J. Tetrahedron 1975, 31, 633-635.
18. (c) Giles, P. R.; Marson, C. M. Tetrahedron Lett. 1990, 31, 5227-5230.
19. (d) Yang, Z.; Liu, H. B.; Lee, C. M.; Chang, H. M.; Wong, H. N. C. J. Org. Chem. 1992, 57, 7248-7257.
20. (e) Kirsch, G.; Prim, D.; Leising, F.; Mignani, G. J. Heterocycl. Chem. 1994, 31, 1005-1010.
21. (f) Prim, D.; Fuss, A.; Kirsch, G.; Silva, A. M. S. J. Chem. Soc., Perkin Trans. 2 1999, 1175-1180.
22. (g) Paul, S.; Gupta, M.; Gupta, R. Synlett 2000, 8, 1115-1118.
23. (h) For the formation of stilbene-type haloalkenes, see ref 3c.
24. 3) δ 1.50 (3H, d, J = 6.96 Hz), 3.82 (3H, s), 3.85 (3H, s), 6.26 (1H, q, J = 6.96 Hz), 6.45 (2H, m), 7.18 (1H, m).
25. (a) Turbomole V5-6. Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H. ; Kölmel, C. Chem. Phys. Lett. 1989, 162, 165-169.
26. (b) Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, 283-290.
27. (c) Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577.
28. (d) Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829-5835.
29. (a) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211.
30. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
31. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
32. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
33. (10) A dielectric constant ∈ of 9 and a solvent radius of 2.3 Å were used. (a) Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799-805. (b) Schäfer, A.; Klamt, A.; Sattel, D.; Lohrenz, J. C. W.; Eckert, F. Phys. Chem. Chem. Phys. 2000, 2, 2187-2193.
34. A dielectric constant ∈ of 9 and a solvent radius of 2.3 Å were used. (a) Klamt, A.; Schüürmann, G. J. Chem. Soc., Perkin Trans. 2 1993, 799-805. (b) Schäfer, A.; Klamt, A.; Sattel, D.; Lohrenz, J. C. W. ; Eckert, F. Phys. Chem. Chem. Phys. 2000, 2, 2187-2193.
35. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
36. (b) Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
37. (a) Jacobs, T. L. In Organic Reactions; Adams, R., Bachmann, W. E., Blatt, A. H., Frieser, L. F., Johnson, J. R., Snyder, H. R., Eds.; John Wiley & Sons, Inc.: New York, 1949; Vol. 5, pp 20-23.
38. (b) Kagan, J.; Arora, S. K.; Bryzgis, M.; Dhawan, S. N.; Reid, K.; Singh, S. P.; Tow, L. J. Org. Chem. 1983, 48, 703-706.
39. Eszenyi, T.; Timar, T.; Sebok, P. Tetrahedron Lett. 1991, 32, 827-828.
40. Kropp, P. J.; Kimberlee, A. D.; Crawford, S. D.; Tubergen, M. W.; Kepler, K. D.; Craig, S. L.; Wilson, V. P. J. Am. Chem. Soc. 1990, 112, 7433-7434.
41. Minato, A.; Suzuki, K., J. Am. Chem. Soc. 1987, 109, 1257-1258.
42. (a) Moughamir, K.; Mezgueldi, B.; Atmani, A.; Mestdagh, H.; Rolando, C. Tetrahedron Lett. 1999, 40, 59-62.
43. (b) Kodomari, M.; Nagaoka, T.; Furusawa, Y. Tetrahedron Lett. 2001, 42, 3105-3107.
44. Fahey, R. C.; Schubert, C. J. Am. Chem. Soc. 1965, 87, 5172-5179.
45. However, the Vilsmeier chloroformylation of 3β-hydroxyandrost-5-en- 17-one gave the ring D chloroalkene as a byproduct. Sciaky, R.; Pallini, U. Gazz. Chim. Ital. 1966, 96, 1241-1253.