Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2011-04-05
2011-04-05
Sullivan, Daniel M (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C568S023000, C568S025000
Reexamination Certificate
active
07919635
ABSTRACT:
Novel substituted phenylsulfur trifluorides that act as fluorinating agents are disclosed. Also disclosed are methods for their preparation and methods for their use in introducing one or more fluorine atoms into target substrate compounds. Finally, various intermediate compounds for use in preparing substituted phenylsulfur trifluorides are provided.
REFERENCES:
patent: 3054661 (1962-09-01), Muetterties
patent: 3919204 (1975-11-01), Boswell, Jr. et al.
patent: 4147733 (1979-04-01), Fiske et al.
patent: 4316906 (1982-02-01), Ondetti et al.
patent: 5055223 (1991-10-01), Reiffenrath et al.
patent: 5093432 (1992-03-01), Bierschenk et al.
patent: 5395916 (1995-03-01), Mochizuki et al.
patent: 5455373 (1995-10-01), Kawa
patent: 5691081 (1997-11-01), Krause et al.
patent: 5741935 (1998-04-01), Bowden et al.
patent: 5789580 (1998-08-01), Chambers et al.
patent: 5824827 (1998-10-01), Bildinov et al.
patent: 6222064 (2001-04-01), Lal et al.
patent: 6737193 (2004-05-01), Umemoto
patent: 6958415 (2005-10-01), Lal et al.
patent: 7015176 (2006-03-01), Bailey, III et al.
patent: 7045360 (2006-05-01), Shair et al.
patent: 7087681 (2006-08-01), Umemoto
patent: 7265247 (2007-09-01), Umemoto et al.
patent: 7381846 (2008-06-01), Umemoto et al.
patent: 7501543 (2009-03-01), Umemoto et al.
patent: 7592491 (2009-09-01), Umemoto
patent: 2004/0022720 (2004-02-01), Low et al.
patent: 2004/0106827 (2004-06-01), Dolbier et al.
patent: 2004/0209854 (2004-10-01), Barkalow et al.
patent: 2004/0249209 (2004-12-01), Bailey, III et al.
patent: 2005/0012072 (2005-01-01), Bailey, III et al.
patent: 2006/0014972 (2006-01-01), Hara et al.
patent: 2009/0105502 (2009-04-01), Umemoto et al.
patent: 2009/0287024 (2009-11-01), Umemoto et al.
patent: 2010/0029992 (2010-02-01), Umemoto et al.
patent: 2010/0076215 (2010-03-01), Umemoto et al.
patent: 2010/0152463 (2010-06-01), Umemoto et al.
patent: 2010/0174096 (2010-07-01), Umemoto et al.
patent: 2010/0234605 (2010-09-01), Umemoto et al.
patent: 0361907 (1990-04-01), None
patent: 1484318 (2004-12-01), None
patent: 227679 (1994-09-01), None
patent: 2276379 (1994-09-01), None
patent: H02-154266 (1990-06-01), None
patent: 2003-077861 (1991-04-01), None
patent: H07-292050 (1995-11-01), None
patent: H09-500893 (1997-01-01), None
patent: 2000-38370 (2000-08-01), None
patent: 2004-359687 (2004-12-01), None
patent: 4531852 (2010-06-01), None
patent: 270111 (1996-02-01), None
patent: I 325857 (2010-06-01), None
patent: I 327135 (2010-07-01), None
patent: WO 03/002553 (2003-01-01), None
patent: WO2004/011422 (2004-02-01), None
patent: WO 2008/013550 (2008-01-01), None
patent: WO 2008/014345 (2008-01-01), None
patent: WO 2008/118787 (2008-10-01), None
patent: WO 2009/076345 (2009-06-01), None
patent: WO 2009/114409 (2009-09-01), None
patent: WO 2010/014665 (2010-02-01), None
patent: WO 2010/022001 (2010-02-01), None
patent: WO 2010/033930 (2010-03-01), None
patent: WO 2010/081014 (2010-07-01), None
Pashinnik et al., {A new method for the synthesis of organosulfur trifluorides, Synthetic Communications (2003), 33(14), 2505-2509}.
Bégué and Bonnet-Delpon (2006). “Recent Advances (1995-2005) in Fluorinated Pharmaceuticals Based on Natural Products” Journal of Fluorine Chemistry 127:992-1012.
Bowden et al. (2000). “A New Method for the Synthesis of Aromatic Sulfurpentafluorides and Studies of the Stability of the Sulfurpentafluoride Group in Common Synthetic Transformations” Tetrahedron 56:3399-3408.
Bunnelle et al. (1990). “Difluorination of Esters. Preparation of α, α-Difluoro Ethers” J. Org. Chem. 55(2):768-770.
Cava and Levinson (1985). “Thionation Reactions of Lawesson's Reagents” Tetrahedron 41(22):5061-5087.
Chambers et al. (1996). “Elemental Fluorine. Part 5.1,2Reactions of 1,3-Dithiolanes and Thioglycosides With Fluorine-Iodine Mixtures” J. Chem. Soc. Perkin Trans. 1 1941-1944.
Cochran (Mar. 19, 1979). “Laboratory Explosions” Chemical & Engineering News 57(19):4.
Feiring (1979). “Chemistry in Hydrogen Fluoride. 7. A Novel Synthesis of Aryl Trifluoromethyl Ethers” J. Org. Chem. 44(16):2907-2910.
Furuya et al. (2005). “Synthesis ofgem-difluorides From Aldehydes Using DFMBA” Journal of Fluorine Chemistry 126:721-725.
Hasek et al. (1960). “The Chemistry of Sulfur Tetrafluoride. II. The Fluorination of Organic Carbonyl Compounds” Journal of American Chem. Soc. 82(3):543-551.
Hayashi et al. (2002). “2,2-Difluoro-1,3-dimethylimidazolidine (DFI). A New Fluorinating Agent” Chem. Commun. 1618-1619.
Henne and Nager (1951). “Trifluoropropyne” J. Am. Chem. Soc. 73(3):1042-1043.
Hoover and Coffman (1964). “Synthesis and Chemistry of Ethynylsulfur Pentafluoride” Journal of Organic Chem. 29:3567-3570.
Huang and Guo (1981). “The Reaction of Arylsulfur Trifluoride With Sterols” Shanghai Institute of Organic Chemistry, ACTA Chimica Sinica 39(1):68.
Kirsch and Bremer (2000). “Nematic Liquid Crystals for Active Matrix Displays: Molecular Design and Synthesis” Angew. Chem. Int. Ed. 39:4216-4235.
Kirsch and Hahn (2005). “Liquid Crystals Based on Hypervalent Sulfur Fluorides: Exploring the Steric Effects of ortho-Fluorine Substituents” Eur. J. of Org. Chem. 3095-3100.
Kobayashi et al.(2004). “Deoxyfluorination of alcohols using N,N-diethyl-α, α-difluoro-(m-methylbenzyl)amine” Tetrahedron 60:6923-6930.
Kuroboshi et al. (1992). “Oxidative Desulfurization-Fluorination of Xanthates. A Convenient Synthesis of Trifluoromethyl Ethers and Difluoro(methylthio)methyl Ethers” Tetrahedron 33(29): 4173-4176.
Kuroboshi and Hiyama (1991). “A Facile Synthesis of Difluoromethylene Compounds by Oxidative Fluorodesulfurization of Dithioacetals Using Tetrabutylammonium Dihydrogentrifluoride andN-Halo Compounds” Synlett 909-910.
Kuroboshi and Hiyama (1992). “A Facile Synthesis of Trifluoromethylamines by Oxidative Desulfurization-Fluorination of Dithiocarbamates” Tetrahedron 33(29):4177-4178.
Kuroboshi and Hiyama (1992). “Oxidative Desulfurization-Fluorination of Methyl Arenedithiocarboxylates. A Convenient Synthesis of Trifluoromethylated Aromatic Compounds” Chemistry Letters 827-830.
Kuroboshi and Hiyama (1994). “A Convenient Synthesis of Perfluoroalkylated Amines by Oxidative Desulfurization-Fluorination” Tetrahedron 35(23):3983-3984.
Kuroboshi and Hiyama (1994). “A Facile Synthesis of α, α-Difluoroalkyl Ethers and Carbonyl Fluoride Acetals by Oxidative Desulfurization-Fluorination” Synlett 251-252.
Lal et al. (1999). “Bis(2-methoxyethyl)aminosulfur trifluoride: a new broad-spectrum deoxofluorinating agent with enhanced thermal stability” Chem. Commun.215-216.
Lal et al. (2000). “Fluorination of Thiocarbonyl Compounds with Bis(2-methoxyethyl)aminosulfur Trifluoride (Deoxo-Fluor Reagent): A Facile Synthesis ofgem-Difluorides” J. Org. Chem. 65:4830-4832.
Lee et al. (1989). “One Pot Phase Transfer Synthesis of O-Alkyl, S-Methyl Dithiocarbonates (Xanthates)” Synthetic Communications 19(3&4):547-552.
Ma and Cahard (2007). “Strategies for Nucleophilic, Electrophilic, and Radical Trifluoromethylations” Journal of Fluorine Chemistry 128:975-996.
Mayer and Scheithauer (1985). Carbonsäuren and Carbonsäure-Derivate E5:891-916.
Middleton (1975). “New Fluorinating Reagents. Dialkylaminosulfur Fluorides” Journal of Organic Chem. 40(5):574-578.
Motherwell and Wilkinson (1991). “Observations on the Reaction of Dithioketals withPara-Iodotoluene Difluoride: A Novel Route togem-Difluoro Compounds” Synlett 191-192.
Olah et al. (1974). “Synthetic Methods and Reactions. I. Selenium Tetrafluoride and Its Pyridine Complex. Convenient Fluorinating Agents for Fluorination of Ketones, Aldehydes, Amides, Alcohols, Carboxylic Acids, and Anhydrides” Journal of American Chem. Soc. 9
Nwaonicha Chukwuma O
Sullivan Daniel M
Swanson & Bratschun L.L.C.
Ube Industries Ltd.
LandOfFree
Substituted phenylsulfur trifluoride and other like... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Substituted phenylsulfur trifluoride and other like..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted phenylsulfur trifluoride and other like... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2711056