A ruthenium-catalyzed, novel and facile procedure for the conversion of vicinal dihaloalkenes to α-diketones [11]

Journal of the American Chemical Society

Volumn 122, Issue 39, 2000, Pages 9558-9559

  Khan, Faiz Ahmed ^a   Prabhudas, B ^a   Dash, Jyotirmayee ^a   Sahu, Nilam ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICARBONYL DERIVATIVE; ALKANE DERIVATIVE; RUTHENIUM;

CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; LETTER; OXIDATION; REACTION ANALYSIS; REACTION TIME;

EID: 0034605445     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001956c     Document Type: Letter

References (50)

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25. Zibuck, R.; Seebach, D. Helv. Chem. Acta 1988, 71, 237-240. Gopal, H.; Gordon, A. J. Tetrahedron Lett. 1971, 2941-2944. Lee, D. J.; Chang, V. S. J. Org. Chem. 1979, 44, 2726-2730. Wolfe, S.; Pilgrim, W. R.; Garrard, T. F.; Chamberlain, P. Can. J. Chem. 1971, 49, 1099-1105. McKillop, A.; Oldenziel, O. H.; Swann, B. P.; Taylor, E. C.; Robey, R. J. Am. Chem. Soc. 1973, 95, 1296-1301.
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29. 4 in which the corresponding carboxylic acids are the exclusive and "normal" products while diketones arc exceptionally formed in two cases for dichloroalkene, see: Huang, B.; Khrapov, M.; Hansen, K. C.; Idoux, J. P.; Gupton, J. T. Synth. Commun. 1995, 25, 2709-2722.
30. Substrates 1 were obtained via Diels-Alder reaction of 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene wilh a series of dienophiles, see: McBee, E. T.; Diveley, W. R.; Burch, J. E. J. Am. Chem. Soc. 1955, 77, 385387. Onishchenko, A. S. Diene Synthesis; Israel program for scientific translation, Jerusalem, 1964. Pews, R. G.; Roberts, C. W.; Hand, C. R. Tetrahedron 1970, 26, 1711-1717. In some cases routine functional group manipulations of the initial adduct furnished the desired substrate. Full details of the new adducts reported here will be published in a full account soon.
31. Substrates 1 were obtained via Diels-Alder reaction of 1,2,3,4- tetrahalo-5,5-dimethoxycyclopentadiene wilh a series of dienophiles, see: McBee, E. T.; Diveley, W. R.; Burch, J. E. J. Am. Chem. Soc. 1955, 77, 385387. Onishchenko, A. S. Diene Synthesis; Israel program for scientific translation, Jerusalem, 1964. Pews, R. G.; Roberts, C. W.; Hand, C. R. Tetrahedron 1970, 26, 1711-1717. In some cases routine functional group manipulations of the initial adduct furnished the desired substrate. Full details of the new adducts reported here will be published in a full account soon.
32. Substrates 1 were obtained via Diels-Alder reaction of 1,2,3,4- tetrahalo-5,5-dimethoxycyclopentadiene wilh a series of dienophiles, see: McBee, E. T.; Diveley, W. R.; Burch, J. E. J. Am. Chem. Soc. 1955, 77, 385387. Onishchenko, A. S. Diene Synthesis; Israel program for scientific translation, Jerusalem, 1964. Pews, R. G.; Roberts, C. W.; Hand, C. R. Tetrahedron 1970, 26, 1711-1717. In some cases routine functional group manipulations of the initial adduct furnished the desired substrate. Full details of the new adducts reported here will be published in a full account soon.
33. Khan, F. A.; Prabhudas, B.; Dash, J. J. Prakt. Chem. 2000. In press.
34. McBee, E. T.; Diveley, W. R.; Burch, J. E. J. Am. Chem. Soc. 1955, 77, 385-387. Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501- 1507. Mehta, G.; Padma, S. Tetrahedron 1991, 47, 7783-7806. Lin, C.-T.; Chou, T.-C. J. Org. Chem. 1990, 55, 2252-2254. Jung, M. E.; Hudspeth, J. P. J. Am. Chem. Soc. 1977, 99, 5508-5510. Sunko, D. E.; Lovrif, Z.; Vanπrik, H. J. Chem. Soc. Chem. Commun. 1985, 1589-1590.
35. McBee, E. T.; Diveley, W. R.; Burch, J. E. J. Am. Chem. Soc. 1955, 77, 385-387. Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501-1507. Mehta, G.; Padma, S. Tetrahedron 1991, 47, 7783-7806. Lin, C.-T.; Chou, T.-C. J. Org. Chem. 1990, 55, 2252-2254. Jung, M. E.; Hudspeth, J. P. J. Am. Chem. Soc. 1977, 99, 5508-5510. Sunko, D. E.; Lovrif, Z.; Vanπrik, H. J. Chem. Soc. Chem. Commun. 1985, 1589-1590.
36. McBee, E. T.; Diveley, W. R.; Burch, J. E. J. Am. Chem. Soc. 1955, 77, 385-387. Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501- 1507. Mehta, G.; Padma, S. Tetrahedron 1991, 47, 7783-7806. Lin, C.-T.; Chou, T.-C. J. Org. Chem. 1990, 55, 2252-2254. Jung, M. E.; Hudspeth, J. P. J. Am. Chem. Soc. 1977, 99, 5508-5510. Sunko, D. E.; Lovrif, Z.; Vanπrik, H. J. Chem. Soc. Chem. Commun. 1985, 1589-1590.
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42. Mehta, G.; Reddy, D. S. Chem. Commun. 1999, 2193-2194. Mehta, G.; Reddy, D. S. Tetrahedron Lett. 1999, 40, 9137-9140. Mehta, G.; Reddy, D. S.; Ramesh, S. S.; Tatu, U. Tetrahedron Lett. 1999, 40, 9141-9144.
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44. For a recent report on cis-dihydroxylation of alkenes using this combination, see: Shing, T. K. M.; Tai, V. W.-F.; Tam, E. K. W. Angew. Chem., Int. Ed. Engl. 1994, 33, 2312-2313. Shing, T. K. M.; Tam, E. K. W.; Tai, V. W.-F.; Chung, I. H. F.; Jiang, Q. Chem. Eur. J. 1996, 2, 50-57.
45. For a recent report on cis-dihydroxylation of alkenes using this combination, see: Shing, T. K. M.; Tai, V. W.-F.; Tam, E. K. W. Angew. Chem., Int. Ed. Engl. 1994, 33, 2312-2313. Shing, T. K. M.; Tam, E. K. W.; Tai, V. W.-F.; Chung, I. H. F.; Jiang, Q. Chem. Eur. J. 1996, 2, 50-57.
46. All new compounds were satisfactorily characterized by spectroscopic methods including elemental analysis.
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49. 4-mediated oxidation of vicinal dichloro alkene, see: Akhtar, I. A.; Fray, G. I.; Yarrow, J. M. J. Chem. Soc. (C) 1968, 812-815. Under these conditions (refluxing acetone), 5a and 16a remained intact and recovered unchanged.
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