Chemistry - Emeritus Faculty

p-Halogenation also offers some of these advantages, in particular regiospecificity, efficiency and safety. The advantages of our approach here is in what we leave out, not what materials we put in. When utilized in tandem, these three protocols present a formidable array of accesses to, in particular, all of the three tri-substituted and all of the three tetra-substituted arrangements of benzene substitution. Each of these unique arrangements exhibit transformable substituents. In other words, each can function as a regiospecific aromatic building block for medicinals, pharmaceuticals, even materials that would demand a particular pattern of aromatic substitution. Above is an example of a 1,2,4,5- tetra-substituted pharmaceutical, ciprofloxacin, which could potentially be regiospecifically synthesized using chemistry developed in our program.

U.S. Patent 3,111,541, Novel Aromatic Sulfides and Method of Preparing Same.
 
Introduction of Substituents at Position 2 of Dimethylaminomethylferrocene through Lithiation. D. W. Slocum, B. W. Rockett and C. R. Hauser, Chemistry and Industry, 1831 (1964).
 
Ring Metalation of Dimethylaminomethylferrocene with Butyllithium and Condensations with Electrophilic Compounds. Synthesis of 1,2-Disubstituted Ferrocenes.  D. W. Slocum, B. W. Rockett and C. R. Hauser, Journal of the American Chemical Society, 87, 1241 (1965).
 
The Absolute Configuration of 2,2'-Dichloro-6-6'-dimethylbiphenyl-4,4'-diamine.  D. W. Slocum and K. Mislow, Journal of Organic Chemistry, 30, 2152 (1965).
 
Magnetic Nonequivalence of Methylene Group Protons in 1,2-Disubstituted Ferrocenes.  P. Smith, J. J. McLeskey, III, and D. W. Slocum, Journal of Organic Chemistry, 30, 4356 (1965).
 
Mass Spectral Fragmentation Patterns of Certain Isomeric Ferrocenes. D. W. Slocum, R. Lewis and G. J. Mains, Chemistry and Industry, 2095 (1966).
 
Reactions of Certain Ferrocene Compounds Leading to a Ferrocenyl Ethyl Ether. D. W. Slocum, B. Silverman, B. W. Rockett and C. R. Hauser, Journal of Organic Chemistry, 32, 464 (1967).
 
Electronic Effects in the Ferrocene Ring System by Proton Magnetic Resonance Spectroscopy.  D. W. Slocum, T. R. Engelmann, R. Lewis and R. J. Kurland, Journal of Chemical and Engineering Data, 13, 378 (1968).
 
Comparative Behavior Upon Lithiation of Dimethylaminomethylferrocene and -Phenethyldimethylamine.  D. W. Slocum, T. R. Engelmann and C. A. Jennings, Australian Journal of Chemistry, 21, 2319 (1968).
 
Reduction of Ferrocene Methiodides with Sodium in Liquid Ammonia; a Route to Alkyl Ferrocenes.  D. W. Slocum and W. Jones, Journal of Organometallic Chemistry, 15, 262 (1968).
 
Metalation of Metallocenes.  D. W. Slocum, T. R. Engelmann, C. R. Ernst, C. A. Jennings, W. E. Jones, B. Koonsvitsky, J. Lewis and P. Shenkin, Journal of Chemical Education, 46, 144 (1969).
 
Reduction of Ferrocene Methiodides; Synthesis of the Dimethylferrocenes.  D. W. Slocum, W. Jones, T. Crimmens and C. R. Hauser, The Journal of Organic Chemistry, 34, 1973 (1969)
 
Ortho Lithiation of N,N-Dimethylbenzenesulfonamide by n-Butyllithium.  Condensation with Electrophilic Compounds.  H. Watanabe, R. A. Schwartz, C. R. Hauser, J. Lewis and D. W. Slocum, Canadian Journal of Chemistry, 47, 1543 (1969).
 
The Coordination Effect of Oxygen in the 2-Metalation of Ferrocenes.  D. W. Slocum and B. P. Koonsvitsky, Chemical Communications, 846 (1969).
 
An Analysis of Diastereotopic Protons in the 2-Halo Dimethylaminomethylferrocenes.  D. W. Slocum and T. R. Engelmann, Journal of Organic Chemistry, 34, 4101 (1969).
 
Fundamental Studies of Substituted Ferrocene Systems. II. Racemization of (+)-1,2(-Ketotetramethylene)fer-rocene.  D. W. Slocum, S. P. Tucker and T. R. Engelmann, Tetrahedron Letters, 621 (1970).
 
Rate and Orientation Effect of TMEDA on Directed Lithiation Reactions.  D. W. Slocum, G. Book and C. A. Jennings, Tetrahedron Letters, 3443 (1970).
 
The Synthesis and Synthetic Utility of 2-Chloromercuridimethylaminomethylferrocene.  D. W. Slocum and T. R. Engelmann, Journal of Organometallic Chemistry, 24, 753 (1970).
 
2-Metalation of Dimethylaminoethylferrocene with Butyllithium and Condensations with Electrophilic Reagents.  Synthesis of 2-Substituted Vinyl Ferrocenes.  D. W. Slocum, C. A. Jennings, T. R. Engelmann, B. W. Rockett and C. R. Hauser, Journal of Organic Chemistry, 36, 377 (1971).
 
Directed Metalation of Certain Thiophene Compounds.  D. W. Slocum and P. L. Gierer, Chemical Communications, 305 (1971).
 
A One-Step Preparation of 1,2-(-Ketotetramethylene)ferrocene.  D. W. Slocum, S. Tucker, J. Davis and T. R. Engelmann, Synthesis in Inorganic and Metalorganic Chemistry, 1, 93 (1971).
 
Metallocene Homoannular Electronic Effects.  D. W. Slocum and C. R. Ernst, Organometallic Chemistry Reviews, Section A, 6, 337 (1970).
 
The Two Faces of D and L Nomenclature.  D. W. Slocum, D. Sugarman and S. P. Tucker, Journal of Chemical Education, 48, 597 (1971).
 
Fundamental Studies of Substituted Ferrocene Systems. III.  Stereochemistry of the Diastereomeric 2,2'-Bis(dimethylaminomethyl)biferrocenyls.  D. W. Slocum and D. I. Sugarman, Tetrahedron Letters, 3287 (1971).
 
Fundamental Studies of Substituted Ferrocene Systems. IV.  Some Aspects of the Contribution of Conformer Population to the Magnetic Nonequivalence of Diastereotopic Nuclei.  D. W. Slocum and F. Stonemark, Tetrahedron Letters, 3291 (1971).
 
Fundamental Studies of Substituted Ferrocenes, I. Electronic Effects of Electron Donating Groups on the Ferrocene System.  D. W. Slocum, P. S. Shenkin, T. R. Engelmann and C. R. Ernst, Tetrahedron Letters, 4429 (1971).
 
Shielding Effects of the Diphenylcarbinol Substituent in Certain Anisole Derivatives: A Method for the Determination of the Site of Metalation.  D. W. Slocum and C. A. Jennings, Chemical Communications, 54 (1972).
 
Directed Metalation Reactions. II.  Demonstration of Directed Lithiation at the 2-Position of Methoxy- and Chloroferrocene.  D. W. Slocum, B. P. Koonsvitsky and C. R. Ernst, Journal of Organometallic Chemistry, 38, 125 (1972).
 
The Concentration Dependence of Hydroxyl Proton Multiplicity in the NMR Spectra of the -Chloroethanols.  D. W. Slocum and C. A. Jennings, Tetrahedron Letters, 3543 (1972).
 
Determination of Intramolecular Hydrogen Bonding in 2-Haloethanols by Methylene Proton Coupling Constant Variations.  C. A. Jennings and D. W. Slocum, Tetrahedron Letters, 3547 (1972).
 
Cyclopentadienyl Complexes of Chromium, Molybdenum and Tungsten.  K. W. Barnett and D. W. Slocum, Journal of Organometallic Chemistry, 44, 1 (1972).
 
The Organic Chemistry of Transition Metal Ligands. I.  Duroquinone.  D. W. Slocum and T. R. Engelmann, Journal of The American Chemical Society, 94, 8596 (1972).
 
Fundamental Studies of Substituted Ferrocene Systems. VI.  Electronic Effects in the Alkylferrocenes.  D. W. Slocum, W. E. Jones and C. R. Ernst, Journal of Organic Chemistry, 37, 4278 (1972).
 
Fundamental Studies of Substituted Ferrocene Systems. V.  Orientation in Electrophilic Substitution of Methoxyferrocene.  D. W. Slocum and C. R. Ernst, Tetrahedron Letters, 5217 (1972).
 
Fundamental Studies of Substituted Ferrocenes. VII.  PMR Resonance Effects in Trimethylsilylferrocene.  D. W. Slocum and C. R. Ernst, Journal of Organic Chemistry, 38, 1620 (1973).
 
Directed Metalation Reactions. III.  Contribution of Oxygen Coordination in the Lithiation of o-t-Butylanisole.  D. W. Slocum and B. P. Koonsvitsky, Journal of Organic Chemistry, 38, 1675 (1973).
 
Directed Metalation Reactions. IV.  2-Metalation of N-Substituted Ferrocene-carboxamides.  D. W. Slocum and F. E. Stonemark, Journal of Organic Chemistry, 38, 1677 (1973).
 
Directed Metalation Reactions. V.  Metalation and Rearrangement in Substituted 2-Thiophenesulfonamides.  D. W. Slocum and P. L. Gierer, Journal of Organic Chemistry, 38, 4189 (1973).
 
Reduction of Ferrocenylmethyl Quaternary Ammonium Iodides: Synthesis of Methylferrocenes.  D. W. Slocum, R. L. Marchal and W. E. Jones.  Journal of Organometallic Chemistry, 72, 227 (1974).
 
Directed Metalation Reactions.  A Specific Route to 1,2,3-Trisubstituted and 1,3-Disubstituted Ferrocenes.  D. W. Slocum, R. L. Marchal and W. E. Jones, Chemical Communications, 967 (1974).
 
Directed Metalation of Model Adrenaline Compounds.  D. W. Slocum and W. Achermann, Chemical Communications, 968 (1974).
 
Directed Metalation Reactions. VI. Competition of Substituents for Ortho Direction of Metalation in Substituted Anisoles.  D. W. Slocum and C. A. Jennings, Journal of Organic Chemistry, 41, 3653 (1976).
 

Directed Metalation Reactions. VII.  Directed Metalation of Methoxymethyl-ferrocene; 2- and 1'-Metalated Ferrocene Intermediates.  D. W. Slocum and B. P. Koonsvitsky, Journal of Organic Chemistry, 41, 3664 (1976).
 
Directed Metalation Reactions. VIII.  Directed Metalation of 3-Mono- and 2,5-Disubstituted Thiophenes.  D. W. Slocum and P. L. Gierer, Journal of Organic Chemistry, 41, 4668 (1976).
 
Tetraphenylborate Zwitterionic Transition Metal Complexes: Stable Homogeneous Catalysts.  D. A. Owen, A. Siegel, R. Lin, D. W. Slocum, B. Conway, M. Moronski and S. Duraj, Annals of the New York Academy of Sciences, 333, 90 (1980).           
 
Synthesis of Ring Substituted Potassium Tetraphenylborate Salts.  D. W. Slocum, S. Duraj and K. Webber, Synthesis and Reactivity in Inorganic and Metal-organic Chemistry, 10, 261 (1980).
 
A Unique Deuterium Exchange Reaction in Certain Substituted Ferrocenes.  D. W. Slocum, D. L. Beach, C. R. Ernst, R. Fellows, M. Moronski, B. Conway and J. Bencini, Chemical Communications, 1043 (1980).
 
The Potential of -Bonded Organometallic Polymers in Catalyst Design.  D. W. Slocum, B. Conway, M. Hodgman, K. Kuchel, M. Moronski, R. Noble, K. Webber and S. Duraj, Journal of Macromolecular Science-Chemistry, 16, 357 (1981).
 
Organometallic Chemistry in the People's Republic of China,  D. W. Slocum and
M. D. Rausch, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 11, 509 (1981).
 
The Preparation of Several N-Substituted and N,N-Disubstituted Ferrocenesulfonamides.  D. W. Slocum and W. Achermann, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 12, 397 (1982).
 
Equilibria Involving Synthesis Gas and Transition Metal Derivatives.  D. W. Slocum, Annals of the New York Academy of Sciences, 415, 314 (1983).
 
Models for Highly Phenylated Transition Metal-containing Polymers; Derivatives of the Pentaphenylcyclopentadienyl Ligand.  D. W. Slocum, S. Johnson, M. Matusz, S. Duraj, J. L. Cmarik, K. M. Simpson and D. A. Owen.  Polymeric Materials Science and Engineering, 49, 353 (1983).
 
Reductive Substitution of Cobaltocene; Displacements of a Cyclopentadienyl Group on Cobaltocene and Replacement of Same by a Diene Moiety.  D. W. Slocum, T. R. Engelmann, R. Fellows, M. Moronski and S. Duraj, Journal of Organometallic Chemistry, 260, C21 (1984).
 
Reductive Substitution of Nickelocene; Interception of a Monohydrido Intermediate in the Hydrogenation of 2,3,4,5-Tetraphenylcyclopentadienone (tetracyclone).  D. W. Slocum, M. Moronski, R. Gooding and S. Duraj, Journal of Organometallic Chemistry, 260, C26 (1984).
 
Substituent Effects on Alkylferrocenes in Molten Salt Mixtures. D. W. Slocum, A. L. Edgecombe, S. Fowler, H. F. Gibbard and J. Phillips, Journal of Organometallic Chemistry, 363, 141 (1989).
 
Substituent Effects on Ferrocenes in Aluminum Chloride/Butyl Pyridinium Chloride Molten Salt Mixtures.  D. W. Slocum, A. L. Edgecombe, J. W. Fowler, H. F. Gibbard and J. Phillips, Organometallics, 9, 307 (1990).
 
Pentaphenylcyclopentadienyl Carbonyl Complexes of Groups VI and VIII Transition Metals.  D. W. Slocum, S. A. Duraj, A. Clearfield, R. Peascoe and M. Matusz, Journal of Macromolecular Science, Chemistry, A27 (9-11), 1405 (1990).
 
New Approaches to the Preparation of Soluble Phthalocyanine Complexes.  M. J. Chen, J. W. Rathke, S. Sinclair and D. W. Slocum.  Journal of Macromolecular Science, Chemistry (invited contribution), A27 (9-11), 1415 (1990).
 
A Predicative Model for Certain Directed Metalations, I; Applications to the Behavior of Anisole.  D. W. Slocum, R. Moon, J. Thompson, D. S. Coffey, J. D. Li, M. G. Slocum, R. Gayton-Garcia and A. Siegel, Tetrahedron Letters, 35, 385 (1994).
 
A Predicative Model for Certain Directed Metalations, II; Applications to the Behavior of p-Fluoroanisole.  D. W. Slocum, D. S. Coffey, A. Siegel and P. Grimes, Tetrahedron Letters, 35, 389 (1994).
 
A Predicative Model for Certain Directed Metalations, III; Methyl Group Influence and Interference in the Directed Metalation of p-Methylanisole (p-MA).  D. W. Slocum, J. Thompson and C. Friesen, Tetrahedron Letters, 36, 8171 (1995).
 
A Predicative Model for Certain Directed Metalations, IV; the Dynamic Behavior of the Organolithio Intermediates formed upon Metalation of p-Dimethoxybenzene (p-DMB).  D. W. Slocum, G. Hayes and N. Kline, Tetrahedron Letters, 36, 8175 (1995).
 
Media Effects in Directed Metalation. D. W. Slocum, D. Reed, F. Jackson, III and C. Friesen, Journal of Organometallic Chemistry, 512, 265 (1996).
 
Ortho-Metalation of p-Chloroanisole: A Media Study. D. W. Slocum and P. Dietzel, Tetrahedron Letters, 40, 1823 (1999).
 
Substrate-promoted ortho-Metalation in Hydrocarbon Solvents. D. W. Slocum, J. Ray and P. Shelton, Tetrahedron  Letters, 43, 6071 (2002).
 
Metalation in Hydrocarbon Solvents:  The Mechanistic Aspects of Substrate-Promoted ortho-   Metalations.  D. W. Slocum, C. Harrison, G. Jackson, R. LaMastus, J. Ray, P. Shelton, A. Walstrom, J. M. Wilcox and R. W. Holman, Tetrahedron  59, 8275 (2003).
 
Metalations in Hydrocarbon Solvents; Media Effects on n-BuLi Reactivity. D. W. Slocum,                   A. Carroll, P. Dietzel, S. Eilerman, J. P. Culver, B. McClure, S. Brown and R. W. Holman, Tetrahedron  Letters, 47, 865 (2006).
 
Metalations Utilizing Aryllithiums; ortho-Functionalization of   p-Bromoanisole (p-BrA).  D.W. Slocum, T. L. Reece, R. D. Sandlin, T. K. Reinscheld and P. E. Whitley, Tetrahedron Letters, 50, 1593 (2009).
 
Metalation of o-Methylanisole (o-MA); an Optional-Site Selectivity Reassessment. D. W. Slocum, Sophia Wang, Christopher B. White and Paul E. Whitley, Tetrahedron, 66, 4939-4942 (2010).
 
Halogen/Lithium Exchange in Hydrocarbon Media; Basic and Continuous Reactor Studies. D. W. Slocum, Damir Kusmic, Jeffrey C. Raber, Thomas K. Reinscheld and Paul E. Whitley, Tetrahedron Letters, 51, 4793-4796 (2010).
 
 p-Iodinations in Hydrocarbon Media. Slocum, D. W.; Telkin, Kristen C.; Nguyen, Quang; Whitley, Paul E.; Fouzia, Begum. Tetrahedron Letters., 52, 7141-7145 (2011).
 
Near Ambient Temperature Halogen/Lithium Exchange of p-Bromoanisole and Related Substrates; Flow/Batch Studies. D. W. Slocum, Thomas K. Reinscheld, Nick D. Austin,  Damir Kusmic and Paul E. Whitley, Synthesis (invited paper), 2531-2536 (2012).
 
Ortho-Lithiations Reassessed: the Advantages of Deficiency Catalysis in Hydrocarbon Media. D. W. Slocum, Thomas K. Reinscheld, Christopher B. White, Michael D. Timmons,  Phillip A. Shelton, Matthew G. Slocum, Rebecca D. Sandlin, Erica G. Holland,  Damir  Kusmic, John A. Jennings, Kristen C. Tekin, Quang Nguyen, Steven J. Bush, Julia M.   Keller and Paul E. Whitley, Organometallics, 32, 1674-1686 (2013).

Electronic Effects in Metallocenes and Certain Related Systems, D. W. Slocum and C. R. Ernst, in "Advances in Organometallic Chemistry," Vol. 10, Academic Press, New York, NY, 1972, pp. 79-114.
 
Carbanions, D. W. Slocum and E. Kaiser, in "Organic Reactive Intermediates," Academic Press, New York, NY, 1973, pp. 337-422.
 
Directed Metalation, D. W. Slocum, and D. Sugarman, in Advances in Chemistry Series, Number 130, "Polyaminechelated Alkali Metal Compounds," A. Langer, editor, American Chemical Society, Washington, D.C., 1974, pp. 222-247.
 
Lithium, Annual Survey covering the year 1973, Journal of Organometallic Chemistry, 95, 1 (1975).
 
Activation of Duroquinone and Potentially Other Dienes via Transition Metal Complexation, D. W. Slocum, T. R. Engelmann, and (in part) R. Fellows, L. Jennings and M. Moronski in "Catalysis in Organic Syntheses, 1977," G. V. Smith, ed., Academic Press, New York, NY, 1977, pp. 175-188.
 
 
Real and Proposed Organometallic -Monomers, D. W. Slocum, M. D. Rausch, and A. Siegel, in "Organometallic Polymers," C. U. Pittman, C. E. Carraher and J. Sheats, eds., Academic Press, New York, NY, 1978, pp. 39-51.
 
Chemicals from Coal: the Cobalt Octacarbonyl Catalyzed Homologation of Methanol to Ethanol, D. W. Slocum, in "Catalysis in Organic Synthesis, 1978," W. Jones, ed., Academic Press, New York, NY, 1980, pp. 245-176.
 
The Role of ⁵  ¹ (  )  Rearranging Cyclopentadienyls in Homogeneous Catalyst Design.  D. W. Slocum, S. Duraj, J. Bencini, K. Webber, R. Noble, K. Kuchel, M. Hodgman, D. A. Owen, A. Siegel and J. Rathke, in "Fundamental Research in Organometallic Chemistry," M. Tsutsui, Y. Ishii, and Y. Z. Yaozeng, editors, Van Nostrand Reinhold Company, New York, NY, and Science Press, Beijing, PRC, 1982, pp. 901-922.
 
The Potential of -Bonded Organometallic Polymers in Catalyst Design.  D. W. Slocum, B. Conway, M. Hodgmen, K. Kuchel, M. Moronski, R. Noble, K. Webber, S. Duraj, A. Siegel and D. A. Owen, in "Organometallic Polymers: Perspectives," C. Carraher, Jr., and J. Sheats, ed., Marcel Dekker, New York, NY, 1982, pp. 357-368.
 
Models for Highly Phenylated -Bonded Transition Metal Containing Polymers;  Chemistry of the  Pentapheylcyclopentadienyl Ligand.  D. W. Slocum, S. Johnson, M. Matusz, S. Duraj, J. L. Cmarik, K. M. Simpson, T. H. Pritchett and D. A. Owen in "Inorganic and Organometallic Polymers," C. Carraher, C. U. Pittman and J. Sheats, eds., Plenum Press, New York, NY, 1985, pp. 59-68.
 
Sections "Metallocenes" and "Organometallic Compound," in Encyclopedia of Science and Technology, McGraw-Hill Book Company, New York, NY, 1987, pp. 53-55 and 519-523, respectively.
 
Sections "Metallocenes" and "Organometallic Compound" in Encyclopedia of Science and Technology, McGraw-Hill Book Company, New York, NY, 1992, pp 50-53 and pp 536-540, respectively.
 
“Metal-halogen Exchange (M  X) of Aryl and Heteroaryl Ring Systems Using Alkyllithiums,” D. W. Slocum, Lithium Link Newsletter, FMC Lithium Division, Gastonia, NC, Winter, 1993.           
 
Section "ortho-Lithioanisole" in Encyclopedia of Reagents for Organic Synthesis, L.A. Paquette, Ed., John Wiley &   Sons, New York, NY, 1995, pp 2970-2973.
 
Section “Metallocenes” in Encyclopedia of Science and Technology, 8th Edition, Volume 11, McGraw-Hill Book   Company, New York, NY, 1997, pp. 61-64.
 
“Halogenation of Intermediate Lithioarenes and Lithiohetarenes,” D. W. Slocum and P. Shelton, Lithium Link   Newsletter, FMC Lithium Division, Gastonia, NC, Fall, 2005.
 
 “Processing Aryllithium and Hetaryllithium Intermediates: Formation of Halogen and Chalcogen Derivatives,”    D. W. Slocum, P. Shelton and K. Moran, Synthesis (invited review) (20) 3477-3498 (2005).
 
“Aryllithiums and Heteryllithiums; Generation and Reactivity” in The Lightest Metals: Science and Technology from Lithium to Calcium, John Wiley and Sons, New York, NY (invited chapter) (22 printed pages - in press), D. W. Slocum.