Efficient synthesis of vinyl chlorides and/or gem-dichlorides from ketones by treatment with tungsten hexachloride

Tetrahedron Letters

Volumn 44, Issue 39, 2003, Pages 7273-7275

  Jung, Michael E ^a   Wasserman, Jacob I ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DICHLOROLISSOCLIMIDE; EPOXIDE; TUNGSTEN DERIVATIVE; TUNGSTEN HEXACHLORIDE; UNCLASSIFIED DRUG; VINYL CHLORIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0041379783     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01884-7     Document Type: Article

References (28)

1. Isolation of dichlorolissoclimide: (a) Malochet-Grivois, C.; Cotelle, P. ; Baird, J. F.; Henichart, J. P.; Debitus, C.; Roussakis, C.; Verbist, J.-F. Tetrahedron Lett. 1991, 32, 6701-6702. Isolation of chlorolissoclimide: (b) Baird, J. F.; Malochet-Grivois, C.; Roussakis, C.; Cotelle, P.; Henichart, J. P.; Debitus, C.; Verbist, J.-F. Nat. Prod. Lett. 1994, 4, 43-50. Crystal structure of dichlorolissoclimide: (c) Toupet, L.; Biard, J. F.; Verbist, J.-F. J. Nat. Prod. 1996, 59, 1203-1204. Biological Activity: (d) Roussakis, C.; Charrier, J.; Riou, D.; Biard, J. F.; Malochet, C.; Meflah, K.; Verbist, J.-F. Anti-Cancer Drug Design 1994, 9, 119-128 and references cited therein.
2. Isolation of dichlorolissoclimide: (a) Malochet-Grivois, C.; Cotelle, P. ; Baird, J. F.; Henichart, J. P.; Debitus, C.; Roussakis, C.; Verbist, J.-F. Tetrahedron Lett. 1991, 32, 6701-6702. Isolation of chlorolissoclimide: (b) Baird, J. F.; Malochet-Grivois, C.; Roussakis, C.; Cotelle, P.; Henichart, J. P.; Debitus, C.; Verbist, J.-F. Nat. Prod. Lett. 1994, 4, 43-50. Crystal structure of dichlorolissoclimide: (c) Toupet, L.; Biard, J. F.; Verbist, J.-F. J. Nat. Prod. 1996, 59, 1203-1204. Biological Activity: (d) Roussakis, C.; Charrier, J.; Riou, D.; Biard, J. F.; Malochet, C.; Meflah, K.; Verbist, J.-F. Anti-Cancer Drug Design 1994, 9, 119-128 and references cited therein.
3. Isolation of dichlorolissoclimide: (a) Malochet-Grivois, C.; Cotelle, P. ; Baird, J. F.; Henichart, J. P.; Debitus, C.; Roussakis, C.; Verbist, J.-F. Tetrahedron Lett. 1991, 32, 6701-6702. Isolation of chlorolissoclimide: (b) Baird, J. F.; Malochet-Grivois, C.; Roussakis, C.; Cotelle, P.; Henichart, J. P.; Debitus, C.; Verbist, J.-F. Nat. Prod. Lett. 1994, 4, 43-50. Crystal structure of dichlorolissoclimide: (c) Toupet, L.; Biard, J. F.; Verbist, J.-F. J. Nat. Prod. 1996, 59, 1203-1204. Biological Activity: (d) Roussakis, C.; Charrier, J.; Riou, D.; Biard, J. F.; Malochet, C.; Meflah, K.; Verbist, J.-F. Anti-Cancer Drug Design 1994, 9, 119-128 and references cited therein.
4. Isolation of dichlorolissoclimide: (a) Malochet-Grivois, C.; Cotelle, P. ; Baird, J. F.; Henichart, J. P.; Debitus, C.; Roussakis, C.; Verbist, J.-F. Tetrahedron Lett. 1991, 32, 6701-6702. Isolation of chlorolissoclimide: (b) Baird, J. F.; Malochet-Grivois, C.; Roussakis, C.; Cotelle, P.; Henichart, J. P.; Debitus, C.; Verbist, J.-F. Nat. Prod. Lett. 1994, 4, 43-50. Crystal structure of dichlorolissoclimide: (c) Toupet, L.; Biard, J. F.; Verbist, J.-F. J. Nat. Prod. 1996, 59, 1203-1204. Biological Activity: (d) Roussakis, C.; Charrier, J.; Riou, D.; Biard, J. F.; Malochet, C.; Meflah, K.; Verbist, J.-F. Anti-Cancer Drug Design 1994, 9, 119-128 and references cited therein.
5. Isolation of reticulidins: (a) Wratten, S. J.; Faulkner, D. J. Tetrahedron Lett. 1978, 16, 1395-1398; (b) Simpson, J. S.; Raniga, P.; Garson, M. J. Tetrahedron Lett. 1997, 38, 7947-7950; (c) Tanaka, J.; Higa, T. J. Nat. Prod. 1999, 62, 1339-1340; (d) Musman, M.; Tanaka, J.; Higa, T. J. Nat. Prod. 2001, 64, 111-113.
6. Isolation of reticulidins: (a) Wratten, S. J.; Faulkner, D. J. Tetrahedron Lett. 1978, 16, 1395-1398; (b) Simpson, J. S.; Raniga, P.; Garson, M. J. Tetrahedron Lett. 1997, 38, 7947-7950; (c) Tanaka, J.; Higa, T. J. Nat. Prod. 1999, 62, 1339-1340; (d) Musman, M.; Tanaka, J.; Higa, T. J. Nat. Prod. 2001, 64, 111-113.
7. Isolation of reticulidins: (a) Wratten, S. J.; Faulkner, D. J. Tetrahedron Lett. 1978, 16, 1395-1398; (b) Simpson, J. S.; Raniga, P.; Garson, M. J. Tetrahedron Lett. 1997, 38, 7947-7950; (c) Tanaka, J.; Higa, T. J. Nat. Prod. 1999, 62, 1339-1340; (d) Musman, M.; Tanaka, J.; Higa, T. J. Nat. Prod. 2001, 64, 111-113.
8. Isolation of reticulidins: (a) Wratten, S. J.; Faulkner, D. J. Tetrahedron Lett. 1978, 16, 1395-1398; (b) Simpson, J. S.; Raniga, P.; Garson, M. J. Tetrahedron Lett. 1997, 38, 7947-7950; (c) Tanaka, J.; Higa, T. J. Nat. Prod. 1999, 62, 1339-1340; (d) Musman, M.; Tanaka, J.; Higa, T. J. Nat. Prod. 2001, 64, 111-113.
9. For a recent example, see: Uddin M.J., Kokubo S., Ueda K., Suenaga K., Uemura D. Chem. Lett. 10:2002;1028-1029. and references cited therein.
10. Tungsten hexachloride has been utilized in several procedures such as the dehydration of epoxides to olefins (Umbreit, M. A.; Sharpless, K. B. Org. Synth. 1981, 60, 29-34) and more recently the chlorination of alcohols (Coe, E. M.; Jones, C. J. Polyhedron 1992, 11, 3123-3128). Also see Ref. 11.
11. Tungsten hexachloride has been utilized in several procedures such as the dehydration of epoxides to olefins (Umbreit, M. A.; Sharpless, K. B. Org. Synth. 1981, 60, 29-34) and more recently the chlorination of alcohols (Coe, E. M.; Jones, C. J. Polyhedron 1992, 11, 3123-3128). Also see Ref. 11.
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14. Representative experimental procedure: To a solution of ketone 4 (0.126 g, 0.50 mmol) in dichloromethane (5 mL) was added tungsten hexachloride (0.397 g, 1.00 mmol) and the solution refluxed (45°C) for 20 min. The reaction mixture was diluted with diethyl ether (25 mL) and poured into 2N sodium hydroxide (15 mL). The organic layer was washed with 2N sodium hydroxide and brine. After drying over magnesium sulfate and filtering to remove the drying agent, the solvent was removed in vacuo to yield vinyl chloride 5 (0.128 g, 0. 47 mmol, 94%) as a reddish oil which solidified under vacuum. The vinyl chlorides could be purified by careful column or thick layer chromatography on silica gel.
15. The structure was also confirmed by an independent synthesis of 5 via treatment of the corresponding known ketoalcohol with methanesulfonic acid and acetyl chloride (Moughamir, K.; Mezgueldi, B.; Atmani, A.; Mestdagh, H.; Rolando, C. Tetrahedron Lett. 1999, 40, 59-62).
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23. This compound has been prepared by chlorination of p-cymene (Tauno, K. Chemosphere 1989, 19, 1349-1356) but never by this type of rearrangement, although bromonitrocamphane undergoes a similar rearrangement to give the bromo analogue. See: (a) McPhail, K. L.; Rivett, D. E. A.; Lack, D. E.; Davies-Coleman, M. T. Tetrahedron 2000, 56, 9391-9396; (b) Ranganathan, S.; Raman, H. H. Tetrahedron 1974, 30, 63-72.
24. This compound has been prepared by chlorination of p-cymene (Tauno, K. Chemosphere 1989, 19, 1349-1356) but never by this type of rearrangement, although bromonitrocamphane undergoes a similar rearrangement to give the bromo analogue. See: (a) McPhail, K. L.; Rivett, D. E. A.; Lack, D. E.; Davies-Coleman, M. T. Tetrahedron 2000, 56, 9391-9396; (b) Ranganathan, S.; Raman, H. H. Tetrahedron 1974, 30, 63-72.
25. This compound has been prepared by chlorination of p-cymene (Tauno, K. Chemosphere 1989, 19, 1349-1356) but never by this type of rearrangement, although bromonitrocamphane undergoes a similar rearrangement to give the bromo analogue. See: (a) McPhail, K. L.; Rivett, D. E. A.; Lack, D. E.; Davies-Coleman, M. T. Tetrahedron 2000, 56, 9391-9396; (b) Ranganathan, S.; Raman, H. H. Tetrahedron 1974, 30, 63-72.
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