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William Dolbier

William Dolbier

Crow Professor, Department of Chemistry, University of Florida

Phone: (352) 392-0591

Fax: (352) 846-1962

Department of Chemistry
PO Box 117200
Gainesville, FL 32611-7200 USA

http://www.chem.ufl.edu/research/facultypage.shtml?photo=dolbier

Education:

Ph.D., Cornell University, 1965

Research Interests:

The Dolbier research program is dedicated mainly to the synthesis and study of compounds containing fluorine. Organic compounds that contain fluorine are of vital interest and importance to virtually every area of modern technology, including polymers, pharmaceutical/agrochemical products, and material science. Because of the special synthetic challenges that it presents, and because of the unique structure/reactivity relationships observed for fluorine-containing compounds, the field of organofluorine chemistry is one of both fundamental and practical interest. In our case this is reflected by the projects in the group, which are a mixture of fundamental and applied projects. Although we remain interested in the fundamental aspects of reactivity of fluorinated molecules and reactive intermediates, our major research interests now involve the development of new synthetic methods for incorporation of fluorine into organic molecules, mainly through the invention and development of new fluorinated "building blocks."

Publications List:

1.Rogelio Ocampo, William R. Dolbier, Jr., Khalil A. Abboud, and Fabio Zuluaga, “Catalyzed Reformatsky Reactions with Ethyl Bromofluoroacetate for the Synthesis of ?-Fluoro-?-hydroxyacids,” J. Org. Chem., 2002, 67, 72-78.

2.William R. Dolbier, Jr., G. Robert Shelton, Merle A. Battiste, John F. Stanton, and David R. Price, “Computational Discovery of a Novel Automerization Process for 1-Fluorocyclopropene,” Org. Lett., 2002, 3, 233-235.

3.Alexander B. Shtarov, Paul J. Krusic, Bruce E. Smart, and William R. Dolbier, Jr., “Use of Gas Phase 1H NMR to Determine the Kinetics of Unimolecular Rearrangement of 2,2-Dichloro-1-methylenecyclopropane and the Bimolecular Dimerization of (Dichloromethylene)cyclopropane,” J. Org. Chem. 2002, 67, 3464-3467.

4.Naoto Takechi, Samia Ait-Mohand, Maurice Medebielle, and William R. Dolbier, Jr., “Nucleophilic Trifluoromethylation of Acyl Chlorides using the Trifluoromethyl Iodide/TDAE Reagent,” Tetrahedron Lett. 2002, 43, 4317-4319.

5.Feng Tian, J. Marshall Baker, Bruce E. Smart, and William R. Dolbier, Jr., “Effect of Fluorine Substitution on the Structure of Oxiranes and on the Energetics of the Oxiranylcarbinyl Radical Ring Opening,” J. Fluorine Chem., 2002, 114, 107-111.

6.Li Zhang, William R. Dolbier, Jr., Brian Sheeler, and Keith U. Ingold, “Absolute Rate Constants of Alkene Addition Reactions of a Fluorinated Radical in Water,” J. Am. Chem. Soc. 2002, 124, 6362-6366.

7.Maurice Medebielle, Katsuya Kato and William R. Dolbier, Jr., “Difluoromethylation Reactions of Ethyl Pyruvate with TDAE. A mild Approach to the Synthesis of 3,3-Difluoro-2-hyroxy-2-methyl-4-oxobutyric Ethyl Ester Derivatives, SynLett 2002, 1541-1543.

8.L. Guyard, P. Audebert, William R. Dolbier Jr., Jian-Xin Duan, “Synthesis and electrochemical polymerization of new oligothiophene functionalized fluorocyclophanes,” J. Electroanal. Chem. 2002, 537, 189-193.

9.Samia Ait-Mohand and William R. Dolbier, Jr., “A New and Convenient Method for Incorporation of Pentafluorosulfanyl (SF5) Substituents Into Organic Compounds,” Org. Lett., 2002, 4, 3013-3015.

10.Merle A. Battiste, Jian-Xin Duan, Yi-An Zhai, Ion Ghiviriga, Khalil A. Abboud, Adrian Roitberg, G. Robert Shelton and William R. Dolbier, Jr., “4,5-Dehydrooctafluoro-[2.2]paracyclophane: Facile Generation and Extraordinary Diels-Alder Reactivity,” Tetrahedron Lett., 2002, 43, 7047-7049.

11.Rogelio Ocampo, William R. Dolbier, Jr., and Fabio Zuluaga, “Synthesis of a-Fluoro-b-lactones,” Collect. Czech. Chem. Commun., 2002, 67, 1325-1334.

12.William R. Dolbier, Jr., Raphaele Romelaer and J. Marshall Baker, “Anomalous Elimination of HCl from 2-Chloro-1,1-difluoroethane. Likely Involvement of a 1,2-FCl Interchange Mechanism,” Tetrahedron Lett., 2002, 43, 8075-8077.

13.William R. Dolbier, Jr., Keith W. Palmer, Feng Tian, Piotr Fiedorow, Andrzej Zaganiaczyk and Henryk Koroniak, “[3.3] Sigmatropic Rearrangement of Some Fluorinated 1,5-Hexadienes,” Collect. Czech. Chem. Commun., 2002, 67, 1517-1532.

14.Naoto Takechi, Samia Ait-Mohand, Maurice Medebielle, and William R. Dolbier, Jr., “Novel Trifluoromethylation of Vicinal Diol Cyclic Sulfates,” Org. Lett., 2002, 4, 4671-4672.

15.Maurice Medebielle, Robert Keyrouz, Bernard Langlois, Thierry Billard, William R. Dolbier, Jr., Conrad Burkholder, Samia Ait-Mohand, Etsuji Okada and Takuro Ashida, “Electron transfer methodologies to the synthesis of organo-fluorine compounds,” in Electron Transfer Reactions in Organic Synthesis, Patrice Vanelle, Ed., Research Signpost, 2002, 91-99.

16.Merle A. Battiste, Feng Tian, John M. Baker, Olivia Bautista, Janette Villalobos, and William R. Dolbier, Jr., “Reactivity and Regiochemical Behavior in the Solvolysis Reactions of 2,2-Difluorocyclopropylcarbinyl Tosylates, J. Fluorine Chem., 2003, 119, 39-51.

17.L. S. Ziemer, S. M. Evans, A. V. Kachur, L. A. Shuman, C. Cardi, W. T. Jenkins, J. S. Karp, A. Alavi, W. R. Dolbier, Jr., and C. J. Koch, “Non-Invasive Imaging of Tumor Hypoxia using the 2-Nitroimidazole [18F]EF5, Eur. J. Nuclear Med., 2003, 30, 259-266.

18.William R. Dolbier, Jr. and Merle A. Battiste, “The Structure, Synthesis and Reactivity of Fluorinated Cyclopropanes and Cyclopropenes,” Chem. Rev., 2003, 103, 1051-1070.

19.Merle A. Battiste, Jian-Xin Duan, Yi-An Zhai, Ion Ghiviriga, Khalil A. Abboud and William R. Dolbier, Jr., “4,5-Dehydro- and 4,5,15,16-bis-(dehydro)octafluoro-[2.2]paracyclophanes: Facile Generation and Extraordinary Diels-Alder Reactivity,” J. Org. Chem., 2003, 68, 3078-3083.

20.William R. Dolbier, Jr., Jian-Xin Duan, Feng Tian, and Qing-Yun Chen, “n-Butyl 2,2-Difluorocyclopropanecarboxylate. Preparation and use of a new difluorocarbene reagent,” Org. Syn., 2003, 80, 172-176.

21.William R. Dolbier, Jr. and William F. Beach, “Parylene-AF4: A Polymer with Exceptional Dielectric and Thermal Properties,” J. Fluorine Chem., 2003, 122, 97-104.

22.William R. Dolbier, Jr. and Yu-Lian Xu, “New synthesis of 3-fluoropyridine derivatives,” J. Fluorine Chem., 2003, 123, 71-73.

23.Maurice Medebielle, Katsuya Kato and William R. Dolbier, Jr., “Fluorinated hydrazones. 1. Reductive coupling reactions of chlorodifluoroacetylated dialkyl hydrazones using TDAE,” Tetrahedron Lett. 2003, 44, 7871-7874.

24.William R. Dolbier, Jr., “Fluorine: A Powerful Tool for Enhancement of Bioactive Compounds. Recent Advances in the Development of CF3 and SF5 Fluorinated Building Blocks,” Chimica Oggi/Chemistry Today, 2003, 21 (5), 66-69. (invited review/editorial).

25. William R. Dolbier Jr., Maurice Medebielle, and Chaya Pooput, A New and Efficient method for the Synthesis of Trifluoromethylthio- and selenoethers, Org. Lett., 2004, 6, 301-304.

26.William R. Dolbier Jr., Feng Tian, Jian-Xin Duan, An-Rong Li, Samia Ait-Mohand, Olivia Bautista, Saiwan Buathong, J. Marshall Baker, Jen Crawford, Pauline Anselme, Xiao Hong Cai, Aneta Modzelewska, Henryk Koroniak, Merle A. Battiste, and Qing-Yun Chen, “Trimethylsilyl fluorosulfonyldifluoroacetate (TFDA). A new, highly efficient difluorocarbene reagent,” J. Fluorine Chem. 2004, 125, 459-469.

27.Li Zhang, Joseph Cradlebaugh, Grzegorz Litwinienko, Bruce E. Smart, Keith U. Ingold and William R. Dolbier, Jr., “Absolute Rate Constants for Some Hydrogen Atom Abstraction Reactions by a Primary Fluoroalkyl Radical in Water,” Org. Biomol. Chem. 2004, 2, 689-694.

28.Xiaohong Cai, Yian Zhai, Ion Ghiviriga, Khalil A. Abboud and William R. Dolbier Jr., “Reactions of TFDA with Ketones. Synthesis of Difluoromethyl 2,2-Difluorocyclopropyl Ethers,” J. Org. Chem. 2004, 69, 4210-4215.

29.Tatiana A. Sergeeva and William R. Dolbier, Jr., “A New Synthesis of Pentafluorosulfanylbenzene,” Org. Lett., 2004, 2417-2419.

30.Joseph A. Cradlebaugh, Li Zhang, G. Robert Shelton, Grzegorz Litwinienko, Bruce E. Smart, Keith U. Ingold, and William R. Dolbier, Jr., “Rate constants for hydrogen abstraction from alkoxides by a perfluoroalkyl radical. An oxyanion accelerated process,” Org. Biomol. Chem., 2004, 2, 2083-2086.

31.Joseph A. Cradlebaugh, Li Zhang, A. B. Shtarev, Bruce e. Smart, and William R. Dolbier, Jr., “ Large primary kinetic isotope effects in the abstraction of hydrogen from organic compounds by a fluorinated radical in water,” Org. Biomol. Chem. 2004, 2, 2087-2091.

32.Rogelio Ocampo and William R. Dolbier, Jr., “The Reformatsky Reaction in Organic Synthesis. Recent Advances,” Tetrahedron, 2004, 60, 9326-9374.

33.Yian Zhai, Ion Ghiviriga, Merle A. Battiste and William R. Dolbier, Jr., “Efficient syntheses of novel naphthaleno- and anthraceno-octafluoro[2.2]paracyclophanes, Synthesis, 2004, 2747-2750.

34.William R. Dolbier, Jr., “Fluorine Chemistry at the Millennium,” J. Fluorine Chem., 2005, in press.

35. William R. Dolbier, Jr., Emilie Gautriaud, and Xiao-Hong Cai, “Competitive kinetic processes in the thermal rearrangement of 1,1-difluoro-2-(dideuteriomethylene)-cyclopropane,” J. Fluorine Chem., 2005, 126, 339-343.

36.Xiaohong Cai, Kai Wu and William R. Dolbier, Jr., “A New synthesis of 2-fluoro-1-naphthols, J. Fluorine Chem., 2005, 126, 479-482.

37.Wei Xu and William R. Dolbier, Jr. “Trifluoromethylation of Imines,” J. Org. Chem. 2005, 70, 4741-4745.

38.Maurice Medebielle, Samia Ait-Mohand , William R. Dolbier, Jr., Conrad R. Burkholder, G. Laumond and Anne-Marie Aubertin, “Syntheses of New Difluoromethylene Benzoxazole and 1, 2, 4-Oxadiazole Derivatives, as Potent Non-nucleoside HIV-1 Reverse Transcriptase Inhibitors,” J. Fluorine Chem. 2005, 126, 535-542.

39.1. G. Kostov, B. Ameduri, T. Sergeeva, W. R. Dolbier, Jr., R. Winter and G. L. Gard, “Original SF5-Containing Fluorinated Copolymers Based on Vinylidene Fluoride,” Macromolecules, 2005, in press.