A Facile, General Approach to the Synthesis of Electrophilic Acetone Equivalents

Journal of Organic Chemistry

Volumn 63, Issue 11, 1998, Pages 3694-3700

  Janicki, Slawomir Z ^a   Fairgrieve, Jennifer M ^a   Petillo, Peter A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004907614     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980094j     Document Type: Article

References (40)

1. De Kimpe, N.; Verhé, R. In The Chemistry of α-haloketones, α-haloaldehydes and α-haloimines; Patai, S., Rappoport, Z., Eds.; J. Wiley & Sons: Chichester, 1988; Chapter 1.
2. De Kimpe, N. In The Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; J. Wiley & Sons: Chichester, 1995; Vol. 1, p 693.
3. Jaohari, R.; Maillard, B.; Filliatre, C.; Villenaue, J. Synthesis 1982, 760.
4. (a) Nakai, T. J. Synth. Org. Chem. Jpn. 1978, 36, 49;
5. (b) Chem. Abstr. 1978, 89, 41560p.
6. Kjonaas, R. A.; Patel, D. D. Tetrahedron Lett. 1984, 25, 5467.
7. (a) Horning, D. E.; Kavadias, G.; Muchowski, M. Can. J. Chem. 1970, 48, 975.
8. (b) Jacobson, R. M.; Raths, R. A.; McDonald, J. H., III. J. Org. Chem. 1977, 42, 2545.
9. Sakurai, H.; Shirahata, A.; Araki, Y.; Hosomi, A. Tetrahedron Lett. 1980, 21, 2325.
10. Greenwood, G.; Hoffman, H. M. R. J. Org. Chem. 1972, 37, 61.
11. (a) Gu, X.-P.; Kirito, Y.; Ikeda, I.; Okahara, M. J. Org. Chem. 1990, 55, 3390.
12. (b) Bresson, A.; Dauphin, G.; Geneste, J.-M.; Kergomard, A.; Lacourt, A. Bull. Chim. Soc. Fr. 1971, 1080.
13. Jacobson, R. M.; Raths, R. A.; McDonald, J. H., III. J. Org. Chem. 1977, 42, 2545.
14. Pyrolysis reactions have been used to synthesize chloroacetone equivalents. See: (a) Gu, X.-P.; Ikeda, I.; Okahara, M. Bull. Chem. Soc. Jpn. 1987, 60, 397. (b) Blanchard L. Bull. Soc. Chim. Fr. 1931, 49, 285. (c) Higgins, R. H.; Eaton, Q. L.; Worth, L.; Peterson, M. V. J. Heterocycl. Chem. 1987, 24, 255. (d) Knapp, S.; Gibson, F. S. J. Org. Chem. 1992, 57, 4802.
15. Pyrolysis reactions have been used to synthesize chloroacetone equivalents. See: (a) Gu, X.-P.; Ikeda, I.; Okahara, M. Bull. Chem. Soc. Jpn. 1987, 60, 397. (b) Blanchard L. Bull. Soc. Chim. Fr. 1931, 49, 285. (c) Higgins, R. H.; Eaton, Q. L.; Worth, L.; Peterson, M. V. J. Heterocycl. Chem. 1987, 24, 255. (d) Knapp, S.; Gibson, F. S. J. Org. Chem. 1992, 57, 4802.
16. Pyrolysis reactions have been used to synthesize chloroacetone equivalents. See: (a) Gu, X.-P.; Ikeda, I.; Okahara, M. Bull. Chem. Soc. Jpn. 1987, 60, 397. (b) Blanchard L. Bull. Soc. Chim. Fr. 1931, 49, 285. (c) Higgins, R. H.; Eaton, Q. L.; Worth, L.; Peterson, M. V. J. Heterocycl. Chem. 1987, 24, 255. (d) Knapp, S.; Gibson, F. S. J. Org. Chem. 1992, 57, 4802.
17. Pyrolysis reactions have been used to synthesize chloroacetone equivalents. See: (a) Gu, X.-P.; Ikeda, I.; Okahara, M. Bull. Chem. Soc. Jpn. 1987, 60, 397. (b) Blanchard L. Bull. Soc. Chim. Fr. 1931, 49, 285. (c) Higgins, R. H.; Eaton, Q. L.; Worth, L.; Peterson, M. V. J. Heterocycl. Chem. 1987, 24, 255. (d) Knapp, S.; Gibson, F. S. J. Org. Chem. 1992, 57, 4802.
18. Yue, C.; Royer, J.; Husson, H.-P. J. Org. Chem. 1992, 57, 4211.
19. Mikolajczyk, M.; Zatorski, A. J. Org. Chem. 1991, 56, 1217.
20. Rigby, J. H.; Moore, T. L.; Rege, S. J. Org. Chem. 1986, 51, 2398.
21. Jaouhari, R.; Maillard, B.; Filliatre, C.; Villenave, J. Synthesis 1982, 760.
22. Schuda, P. F.; Bernstein, B. Synth. Commun. 1984, 14, 293.
23. Brouwer, M. S.; Hulkenberg, A.; Kok, J. G. J.; van Moorselaar, R.; Overbeek, W. R. M.; Wesselman, P. G. J. Recueil 1979, 98, 316.
24. Hambly, G. H.; Chan, T. H. Tetrahedron Lett. 1986, 27, 2563.
25. Kruglaya, O. A.; Belousova, L. I.; Gendin, D. V.; Kalikhman, I. D. J. Organomet. Chem. 1980, 201, 69.
26. Hosomi, A.; Shirahata, A.; Araki, Y.; Sakurai, H. J. Org. Chem. 1981, 46, 4631.
27. Gu, X.-P.; Nobuyuki, N.; Ikeda, I.; Okahara, M. J. Org. Chem. 1987, 59, 3109.
28. Blanchard, L. Bull. Soc. Chim. Fr. 1926, 39, 1265. Ikeda, I.; Ohsuka, A.; Tani, K.; Hirao, T.; Rurosawa, H. J. Org. Chem. 1996, 61, 4971.
29. Blanchard, L. Bull. Soc. Chim. Fr. 1926, 39, 1265. Ikeda, I.; Ohsuka, A.; Tani, K.; Hirao, T.; Rurosawa, H. J. Org. Chem. 1996, 61, 4971.
30. Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155. Iqbal, J.; Khan, M. A.; Srivastava, R. R. Tetrahedron Lett. 1988, 29, 4985. Shibata, I.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1986, 27, 3021. Kotsuki, H.; Ichikawa, Y.; Nishizawa, H. Chem. Lett. 1988, 673.
31. Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155. Iqbal, J.; Khan, M. A.; Srivastava, R. R. Tetrahedron Lett. 1988, 29, 4985. Shibata, I.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1986, 27, 3021. Kotsuki, H.; Ichikawa, Y.; Nishizawa, H. Chem. Lett. 1988, 673.
32. Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155. Iqbal, J.; Khan, M. A.; Srivastava, R. R. Tetrahedron Lett. 1988, 29, 4985. Shibata, I.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1986, 27, 3021. Kotsuki, H.; Ichikawa, Y.; Nishizawa, H. Chem. Lett. 1988, 673.
33. Iqbal, J.; Srivastava, R. R. Tetrahedron 1991, 47, 3155. Iqbal, J.; Khan, M. A.; Srivastava, R. R. Tetrahedron Lett. 1988, 29, 4985. Shibata, I.; Baba, A.; Matsuda, H. Tetrahedron Lett. 1986, 27, 3021. Kotsuki, H.; Ichikawa, Y.; Nishizawa, H. Chem. Lett. 1988, 673.
34. Takeda, T.; Yasuhara, S.; Watanabe, S. Bull. Chem. Soc. Jpn. 1980, 53, 2566.
35. Daukahas, V. K.; Ramanauskas, Yu. Yu.; Brukshtus, A. B.; Dundene, G. V.; Udrenaite, E. B.; Yautakene, I. Yu. Pharm. Chem. J. (Engl. Transl.) 1990, 24, 731. Beger, J.; Schiefer, H. J. Prakt. Chem. 1980, 322, 3039.
36. Daukahas, V. K.; Ramanauskas, Yu. Yu.; Brukshtus, A. B.; Dundene, G. V.; Udrenaite, E. B.; Yautakene, I. Yu. Pharm. Chem. J. (Engl. Transl.) 1990, 24, 731. Beger, J.; Schiefer, H. J. Prakt. Chem. 1980, 322, 3039.
37. Nucleophilic displacements on 12 have been previously reported: (a) Mamedov, S.; Gadzhizade, F.; Sharifova, F.; Koval'skaya, I. J. Gen. Chem. USSR (Engl. Transl.) 1964, 34, 2900.
38. We typically fractionally distill 25 under reduced pressure at least three times. This is the rate-limiting step in the procedure. Once purified, 25 is stable for months at -20 °C and can be used without further purification.
39. Köbrich, G.; Buck, P. Chem. Ber, 1970, 103, 1412.
40. The report on 0.5 mol scale synthesis of 6 is being prepared for publication. Chong, P. C.; Janicki, S. Z.; Petillo, P. A. Org. Synth. Manuscript in preparation.