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Richard V. Williams

Richard V. Williams

Professor

Office

Renfrew Hall 313E

Mailing Address

Department of Chemistry
875 Perimeter Dr, MS 2343
Moscow, ID 83844-2343

  • Some uses of Silicon Compounds in Organic Synthesis, Ph.D. Thesis, Cambridge, 1978.
  • R. H. Mitchell, Y.-H. Lai, and R. V. Williams, "N-Bromosuccinimide Dimethylformamide: A Mild, Selective Nuclear Mono-Bromination Reagent for Reactive Aromatic Compounds." J. Org. Chem., 1979, 44, 4733.
  • I. Fleming and R. V. Williams, "The Reaction between bis(trimethylsilyl)- cyclopentadiene and Dichloroketen, and the Diels-Alder Reactions between N-Phenylmaleimide and Two Silylated Methylcyclopentadienes," J.C.S. Perkin, I 1981, 684.
  • L. A. Paquette and R. V. Williams, "Silicon in Organic Synthesis.12. trans-1- Benzenesulfonyl-2-(Trimethylsilyl)ethylene, A Diels-Alder Dienophile Equivalent of Acetylene and Monosubstituted Acetylenes," Tetrahedron Letters, 1981, 22, 4643.
  • R. H. Mitchell, R. V. Williams, and T. W. Dingle, "Toward the Understanding of Benzannelated Annulenes: Synthesis and Properties of [a,h]- and [a,i]-Ring Dibenzannelated Dihydropyrenes," J. Am. Chem. Soc., 1982, 104, 2560.
  • R. H. Mitchell, R. V. Williams, R. Mahadevan, Y.-H. Lai, and T. W. Dingle, "Toward the Understanding of Benzannelated Annulenes: A Simple Correlation of the Diatropicity of Several Benzannelated Dihydropyrenes in terms of Bond Order Deviations with Predictions for Other Benzannulenes," J. Am. Chem. Soc., 1982, 104, 2571.
  • L. A. Paquette, R. V. Williams, R. V. C. Carr, P. Charumilind, and J. F. Blount, "[1,5]Hydrogen Sigmatropy within Isodicyclopentadiene. Cycloadditive Capture of a Fleeting Isomer with Dienophiles of Low Reactivity," J. Org. Chem., 1982, 47, 4566.
  • R. H. Mitchell, T. W. Dingle, P. R. West, R. V. Williams, and R. C. Thompson, "On the Possibility of New Families of (4n+2) Electron Biradicaloid Hydrocarbons," J. Org. Chem., 1982, 47, 5210.
  • R. H. Mitchell, T. W. Dingle, and R. V. Williams, "2,3-Dimethylnaphthalene/TMEDA/n-Butyllithium: An Unusual Ambident Aromatic Nucleophile," J. Org. Chem., 1983, 48, 903.
  • L. A. Paquette, A. R. Browne, C. W. Doecke, and R. V. Williams, "A Short Stereocontrolled Synthesis of [4]Peristylane," J.Am. Chem. Soc., 1983, 105, 4113.
  • A. J. Fry, J. Simons, M. Tashior, T. Yamato, R. H. Mitchell, T. W. Dingle, R. V. Williams, and R. Mahadevan, "Electrochemical Reduction of Substituted 15,16-Dihydropyrenes in Dimethylformamide," Acta Chem. Scand., 1983, 837, 445.
  • R. V. C. Carr, R. V. Williams, and L. A. Paquette, "Dienophilic Properties of Phenylvinyl Sulfone and trans-1-Benzenesulfonyl-2-(trimethylsilyl)-ethylene. Their Utilization as Synthons
    for Ethylene, 1-Alkenes, Acetylene, and Monosubstituted Alkynes in the Construction of Functionalized Six-membered Rings via [4+2] Cycloaddition Methodology," J. Org. Chem., 1983, 48, 4976.
  • R. H. Mitchell, P. D. Slowey, T. Kamada, R. V. Williams, and P. J. Garratt, "The Mills- Nixon Effect - A resolution: Clear evidence for no significant bond localization in small ring annelated aromatics. The Synthesis and diatropicity of cyclobutane annelated dihydropyrenes," J. Am. Chem. Soc., 1984, 106, 2431.
  • L. A. Paquette, R. V. Williams, M. Vazeux, and A. R. Browne, "Factors Conducive to the Cascade Rearrangement of Sterically Congested and Geometrically Restricted Three-Membered Rings. Facile Synthesis of a Topologically Nonplanar Heterocycle," J. Org. Chem., 1984, 49, 2194.
  • R. H. Mitchell, M. Chaudhary, T. W. Dingle, and R. V. Williams, "Unusual macrocyclic biphenyls containing the dihydropyrene nucleus. An observation of aryl group transfer from phosphine to aryl halide using nickel complexes," J. Am. Chem. Soc., 1984, 106, 7776.
  • R. V. Lloyd, and R. V. Williams, "The bridgehead decalin radicals: Evidence for non- planarity at the radical site," J. Phys. Chem., 1985, 89, 5379.
  • R. H. Mitchell, T. K. Vinod, G. J. Bodwell, K. S. Weerawarna, W. Anker, R. V. Williams, and G. W. Bushnell, "A fusion of Metals, Cyclophanes, and Dihdropyrenes," Pure and Applied Chemistry, 1986, 58, 15.
  • R. H. Mitchell, M. Chaudhary, T. Kamada, P. D. Slowey and R. V. Williams, "cis- Dimethyldihydropyrene synthesis: an approach utilising a Diels-Alder route to 1,2,3- trisubstituted benzenes," Tetrahedron, 1986, 42, 1741.
  • H. A. Kurtz, R. V. Lloyd, and R. V. Williams, "The Bridgehead Decalin Radicals: An MM2 and MNDO Study," J. Org. Chem., 1987, 52, 302.
  • R. V. Williams, and C.-L.A. Sung, "The Unexpected Regio and Stereospecific Diels- Alder Reaction between Cyclopentadiene and 2-Benzenesulphonyl-3- trimethylsilylbicyclo[2.2.1]hepta-2,5-diene," J. Chem. Soc., Chem. Commun., 1987, 590.
  • P. C. B. Page, S. Rosenthal, and R. V. Williams, "Acyl Silanes as Synthetic Intermediates: Formation of Acyl Anions and Unusual Fluoride initiated Silicon to Carbon Alkyl Group Migration," Tetrahedron Letters, 1987, 28, 4455.
  • R. V. Williams, C.-L. A. Sung, H. A. Kurtz, and T. M. Harris, "Experimental evidence establishing an upper limit to the activation barrier for the butterfly bending of the double bond in anti-sesquinorbornene," Tetrahedron Letters, 1988, 29, 19.
  • P. C. B. Page, S. Rosenthal, and R. V. Williams, "A new, one-pot synthesis of primary 2- Alkynamides" Synthesis, 1988, 621.
  • R. V. Williams, and H. A. Kurtz, "The quest for a neutral homoaromatic hydrocarbon. The MNDO study of Pentacyclo[7.2.1.04,11.06,9.06,10]dodeca-1,4-diene an annelated semibullvalene derivative" J. Org. Chem., 1988, 53, 3626.
  • R. V. Williams, H. A. Kurtz, and B. Farley, "The use of semiempirical energy partitioning terms in the study of through space (homoaromatic) interactions," Tetrahedron, 1988, 44, 7455.
  • R. V. Williams, W. J. Ebey, X. Ji, and D. van der Helm, "The Crystal Structures of Different Diastereomers of 2-benzenesulfinylbicyclo[2.2.1]hept-5-ene. C7H9SOC6H5". Acta Cryst. 1989, B45, 93
  • R. V. Williams, and X. Lin, "New Ketene Equivalents for the Diels-Alder Reaction. Vinyl Sulphoxide Cycloadditions," J. Chem. Soc., Chem. Commun., 1989, 1872.
  • R. V. Williams, G. W. Kelley, D. van der Helm, J. Loebel, and P. B. C. Page, "Experimental Evidence for the Lack of Stereoselectivity in the Electrophilic Quench of Sulfonyl Carbanions," J. Org. Chem., 1990, 55, 3840.
  • R. V. Williams, and K. Chauhan, "New Allene Equivalents for the Diels-Alder Reaction: Vinyl Sulphoxide Cycloadditions," J. Chem. Soc., Chem. Commun., 1991, 1672.
  • R. H. Mitchell, M. Chaudhary, R. V. Williams, R. Fyles, J. Gibson, M. Ashwood-Smith, and A. J. Fry, "Straining Strained Molecules. III. The Spectral and Mutagenic Properties and an Alternate Synthesis of Diaceperylene and Dicyclopenta[1,2,3-cd:1',2',3'-lm]perylene," Can. J. Chem., 1992, 70, 1015.
  • R. V. Williams, M.M.R. Todime, P. Enemark, D. van der Helm, and S.K. Rizvi, "Unusual Stereoselectivity in the Diels-Alder Addition of Cyclopentadiene with the Bicyclo[2.2.2]octene Nucleus," J.Org..Chem., 1993, 58, 6740.
  • R. V. Williams, and H. A. Kurtz, "Homoaromaticity," Advances in Phys. Org. Chem, 1994, 29, 273.
  • R. V. Williams and H. A. Kurtz, "A Theoretical Investigation of Through Space Interactions. Part 3 The Semi-Empirical Study of the Cope Rearrangement in Singly Annelated Semibullvalenes," J. Chem. Soc., Perkin Trans., 2, 1994, 147.
  • R. V. Williams, K. Chauhan, and V. R. Gadgil, "1-Benzenesulphonyl-2- trimethylsilylacetylene: A New Acetylene Equivalent for the Diels-Alder Reaction," J. Chem. Soc., Chem. Commun., 1994, 1739.
  • R. V. Williams, V. R. Gadgil, K. Chauhan, D. van der Helm, M. B. Hossain, L. M. Jackman, and E. Fernandes, “1,5-Dimethyl-2,4,6,8-semibullvalenetetracarboxylic Dianhydride:
    - A Close Approach to a Neutral Homoaromatic Semibullvalene,” J. Am. Chem. Soc., 1996, 118,4208.
  • J. H. Cooley and R. V. Williams, “Endo and Exo Stereochemistry in the Diels-Alder Reaction; Kinetic Versus Thermodynamic Control,” J. Chem. Educ, 1997, 74, 582.
  • R. V. Williams, V. R. Gadgil, A. Vij, J. M. Cook, Q. Huang, and G. Kubiak, “Unexpected Stereoselectivity in the Weiss-Cook Condensation of Dimethyl 1,3- Acetonedicarboxylate with 2,3-Pentanedione,” J. Chem. Soc., Perkin Trans. 1, 1997, 1425.
  • H. Jiao, R. Nagelkerke, H. A. Kurtz, R. V. Williams, W. T. Borden, and P. von R. Schleyer, “Annelated Semibullvalenes: A Theoretical Study of How They "Cope" with Strain,” J. Am. Chem. Soc., 1997, 119, 5921.
  • R. V. Williams, W. D. Edwards, A. Vij, R. W. Tolbert, and R. H. Mitchell, “A Theoretical Study and X-ray Structure Determination of Dimethyldihydropyrene,” J. Org. Chem., 1998, 63, 3125.
  • R. V. Williams, V. R. Gadgil, K. Chauhan, L. M. Jackman, and E. Fernandes, “The Search for Homoaromatic Semibullvalenes. Part 5.1 1,5-Dimethyl-2,4,6,8- semibullvalenetetracarboxylic Dianhydride,” J. Org. Chem., 1998, 63, 3302.
  • R. V. Williams, W. D. Edwards, V. R. Gadgil, M. E. Colvin, E. T. Seidl, D. van der Helm and M. B. Hossain “Pyramidalized Olefins : Ab Initio Study and X-ray Structure Determination of Bicyclo[2.2.2]octadienes,” J. Org. Chem., 1998, 63, 5268.
  • R. V. Williams, “Semibullvalenes - Homoaromatic Bovines?” Adv. Theor. Interesting Mol. 1998, 4, 157.
  • R. V. Williams, V. R. Gadgil, P. Luger, T. Koritsanszky, and M. Weber, “The Search for Homoaromatic Semibullvalenes. Part 6.1 X-Ray Structure and Charge Density Studies of 1,5- Dimethyl-2,4,6,8-semibullvalenetetracarboxylic Dianhydride in the Temperature Range 123-15 K,” J. Org. Chem. 1999, 64, 1180.
  • R. V. Williams, V. R. Gadgil, G. G. Garner, J. D. Williams, and A. Vij, “Pyramidalized Olefins: The Stereospecific Conjugate Reduction of a Bicyclo[2.2.2]octadiene,” Tetrahedron Lett. 1999, 40, 2689.
  • J. H. Cooley and R. V. Williams, “Qualitative Analysis in the Beginning Organic Laboratory,” J. Chem. Educ. 1999, 76, 1117.
  • R. V. Williams, M. E. Colvin, N. Tran, R. N. Warrener and D. Margetic, “Exceptionally Pyramidalized Olefins: A Theoretical Study of the Cyclopropenyl Fused Tricycles - Tricyclo[3.2.1.02,4]oct-2(4)-ene, Tricyclo[3.2.1.02,4]octa-2(4),6-diene, Tricyclo[3.2.2.02,4]non- 2(4)-ene and Tricyclo[3.2.2.02,4]nona-2(4),6-diene,” J. Org. Chem. 2000, 65, 562.
  • A. Vij, J. L. Palmer, K. Chauhan, and R. V. Williams, “The Role of Hydrogen Bonding in Pseudo-Macrocyclic Ring Formation in 2,6-dimethyl-1,3,5,7-cyclooctatetraene-1,3,5,7- tetracarboxylic Acid Monohydrate,” J. Chem. Cryst. 2000, 30, 621.
  • R. V. Williams, “Semibullvalenes and Related Molecules: Ever Closer Approaches to Neutral Homoaromaticity,” Eur. J. Org. Chem. 2001, 227.
  • M. Heubes, T. Dietz, H. Quast, M. Seefelder, A. Witzel, V. R. Gadgil, and R. V. Williams, “Lifting of the Degeneracy in Semibullvalenes by Remote and Direct Substituents: A Quantitative Study Using Variable-Temperature Carbon-13 NMR Spectroscopy,” J. Org. Chem. 2001, 66, 1949.
  • R. V. Williams, “Homoaromaticity” Chem. Rev. 2001, 101, 1185.
  • R. V. Williams, J. R. Armantrout, B. Twamley, R. H. Mitchell, T. R. Ward and S. Bandyopadhyay, “A Theoretical and Experimental Scale of Aromaticity. The First Nucleus- Independent Chemical Shifts (NICS) Study of the Dimethyldihydropyrene Nucleus,” J. Am. Chem. Soc. 2002, 124, 13495.
  • U. Majumder, J. R. Armantrout, R. V. Williams and J. M. Shreeve “N, N-Difluorotris(t- butyl)silyl Amine - The First Organosilyl Difluoroamine. Synthesis and Computational Studies,” J. Org. Chem. 2002, 67, 8435.
  • D. B. Kimball. M. M. Haley, R. H. Mitchell, T. R. Ward, S. Bandyopadhyay R. V. Williams and J. R. Armantrout, “Dimethyldihydropyrene-Dehydrobenzoannulene Hybrids: Studies in Aromaticity and Photoisomerization,” J. Org. Chem. 2002, 67, 8798.
  • A. J. Boydston, M. M. Haley, R. V. Williams and J. R. Armantrout, “Diatropicity of 3,4,7,8,9,10,13,14-Octadehydro[14]annulenes: A Combined Experimental and Theoretical Investigation,” J. Org. Chem. 2002, 67, 8812.
  • S. Samdal, A. D. Richardson, K. Hedberg, V. R. Gadgil, M. M. Meyer and R. V. Williams, “Gas-Phase Electron-Diffraction Investigation and Quantum-Chemical Calculations of the Structure of 1,5-Dimethylsemibullvalene-2,4,6,8-tetracarboxylic Dianhydride,” Helv. Chim. Acta 2003, 86, 1741.
  • J. H. Cooley and R. V. Williams, “The Pyrolysis of Polystyrene,” Chem. Educator [Online] 2003, 8, 1; DOI 10.1333/s00897030720a
  • D. Margetic, R. V. Williams and R. N. Warrener, “Pyramidalized Olefins: A DFT Study of the Homosesquinorbornene and Sesquibicyclo[2.2.2]octane Nuclei,” J. Org. Chem. 2003, 68, 9186.
  • R. V. Williams and D. Margetić, “Pyramidalized Olefins: A DFT Study of bicyclo- [2.1.1], -[3.2.1] and -[3.2.2] Alkenes and their Fused Derivatives. Two Rare Examples of Facially Symmetric Pyramidal Olefins,” J. Org. Chem. 2004, 69, 7134.
  • R. H. Mitchell , R. Blunden , G. Hollett , S. Bandyopadhyay , R. V. Williams , B. Twamley, “13-Methyl-2,6-dithia[7]metacyclophane - A Useful Molecule to Connect VT NMR Results and Structure with Calculations,” J. Org. Chem. 2005, 70, 675.
  • D. A. Hrovat, E. C. Brown, R. V. Williams, H. Quast, W. T. Borden, “How Important Is Bishomoaromaticity in Determining the Relative Barrier Heights for the Degenerate Cope Rearrangements of Semibullvalene, Barbaralane, Bullvalene and Dihydrobullvalene?” J. Org. Chem. 2005, 70, 2627.
  • M. Seefelder, M. Heubes, H. Quast, W. D. Edwards, J. R. Armantrout, R. V. Williams, C.J. Cramer, A. C. Goren, D. A. Hrovat and W. T. Borden “An Experimental and Theoretical Study of Stabilization of Delocalized Forms of Semibullvalenes and Barbaralanes by Dipolar and Polarizable Solvents. Observation of a Delocalized Structure that is Lower in Free Energy than the Localized Form,” J. Org. Chem. 2005, 70, 3437
  • R. V. Williams, W. D. Edwards, R. H. Mitchell and S. G. Robinson “A DFT Study of the Thermal, Orbital Symmetry Forbidden, Cyclophanediene to Dihydropyrene Electrocyclic Reaction. Predictions to Improve the Dimethyldihydropyrene Photoswitches,” J. Am. Chem. Soc. 2005, 127, 16207.
  • T. Yoshimura, A. Inaba, M. Sonoda, K. Tahara, Y. Tobe and R. V. Williams “Synthesis and Properties of Trefoil-Shaped Tris(hexadehydrotribenzo[12]annulene) and Tris(tetradehydrotribenzo[12]annulene),” Org. Lett. 2006, 8, 2933.
  • K. Tahara, T. Yoshimura, M. Sonoda, Y. Tobe and R. V. Williams “Theoretical Studies on Graphyne Substructures: Geometry, Aromaticity and Electronic Properties of the Multiply Fused Dehydrobenzo[12]annulenes,” J. Org. Chem. 2007, 72, 1437.
  • K. Ayub, R. Zhang, S. G. Robinson, B. Twamley, R. V. Williams and R. H. Mitchell “Suppressing the Thermal Metacyclophaneto Dihydropyrene Isomerization: Synthesis and Rearrangement of 8,16-Dicyano[2.2]metacyclophane-1,9-diene and Evidence Supporting the Proposed Biradicaloid Mechanism,” J. Org. Chem. 2008, 73, 451.
  • R. H. Mitchell, R. Zhang, D. J. Berg, B. Twamley and R. V. Williams “Measuring Aromaticity with the Dimethyldihydropyrene Ring Current Probe. Experimental and Calculational Studies of the Fulvenes and the Strongly Antiaromatic Cyclopentadienone Reveal Large Mills-Nixon Type Bond Localization Effects. Synthesis of Fulvene Fused Dihydropyrenes,” J. Am. Chem. Soc. 2009, 131, 189.
  • R. V. Williams “Molecules with Labile Bonds: Selected Annulenes and Bridged Homotropilidenes,” invited chapter in “Strained Hydrocarbons” ed. H. Dodziuk, Wiley-VCH, 2009.
  • K. Ayub, R. Li, C. Bohne, R. V. Williams and R. H. Mitchell, “Calculation Driven Synthesis of an Excellent Dihydropyrene Negative Photochrome and its Photochemical Properties,” J. Am. Chem. Soc. 2011, 133, 4040.
  • P. R. Griffiths, D. E. Pivonka and R. V. Williams, “The Experimental Realization of a Neutral Homoaromatic Carbocycle,” Chem. Eur. J. 2011, 17, 9193.
  • R. H. Mitchell, P. Zhang, D. J. Berg and R. V. Williams, “An Experimental Estimate of the Relative Aromaticity of the Cyclooctatetraene Dianion by Fusion to Dimethyldihydropyrene,” Chem. Commun., 2012, 48, 8144.
  • R. V. Williams, W. D. Edwards, P. Zhang, D. J. Berg and R. H. Mitchell, “Experimental Verification of the Homoaromaticity of 1,3,5-Cycloheptatriene and the Evaluation of the Aromaticity of Tropone and the Tropylium Cation Using the Dimethyldihydropyrene Probe,” J. Am. Chem. Soc., 2012, 134, 16742.
  • T. C. Nugent, R. V. Williams, A. Dragan, A. V. Iosub, and A. A. Méndez, “An Investigation of the Observed, but Counter-Intuitive, Stereoselectivity Noted During Chiral Amines Synthesis via N-Chiral-Ketimines,” Beilstein J. Org. Chem., 2013, 9, 2103.
  • R. V. Williams*, A. J. Aring, M. C. Bonifacio and A. Blumenfeld, “4,6- Barbaralanedicarboxy-2,8-dicarboxylic Anhydride and 4,6-Barbaralanedicarboxy-2,8- dicarboxylic Anhydride: Examples of Unusual Barbaralanes and Semibullvalenes that Do Not Undergo the Cope Rearrangement. They are locked as the Closed Tautomers.” J. Phys. Org. Chem. 2017, 30, DOI: 10.1002/poc.3622.
  • R. V. Williams* and A. A. Shaffer, “Writing Reaction Mechanisms. The Use of Site- Specific Curly Arrows as an Aid to Comprehension.” Can. J. Chem. 2017, 95, 334
  • R. V. Williams, A. G. Al-Sehemi, A. K. Meier, Z. Z. Brown and J. R. Armantrout, “The Role of Strain in the Homoaromatization of Semibullvalenes,” J. Org. Chem., 2017, 82, 4136.
  • A. Canul, D. Thapa, J. Huso, L. Bergman, R. V. Williams and R. Machleidt, “Mixed- Strategy Approach to Band-Edge Analysis and Modeling in Semiconductors.” Phys. Rev. B, 2020, 101, 195308.

Department of Chemistry

Physical Address:
Renfrew Hall 116

Mailing Address:
875 Perimeter Dr, MS 2343
Moscow, ID 83844-2343

Phone: 208-885-6552

Fax: 208-885-6173

Email: chemoff@uidaho.edu

Web: Department of Chemistry