Group Publications

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  • Bartelson, A. B.; Lambert, K. M.; Bobbitt, J. M.; BAILEY, W.F. Recent Developments in the Nitroxide-Catalyzed Oxidation of Amines: Preparation of Imines and Nitriles. Chem. Cat. Chem. Accepted Article; DOI: 10.1002/cctc.201600858. [LINK]

Picture4

  • BAILEY, W.F.; Fair, J. D. Regioselective Lithium–Iodide Exchange-Initiated Cleavage of 2-Iodo-1,3-dioxanes: A Complex -Induced Proximity Effect. J. Org. Chem. 81, 3951-3955. [LINK]

Picture3

  • Lambert, K. M.; Bobbitt, J. M.; Eldirany, S. E.; Kissane, L. E.; Sheridan, R. K.; Stempel, Z. S.; Sternberg, F. H; BAILEY, W. F. Metal-Free Oxidation of Primary Amines to Nitriles Through Coupled Catalytic Cycles. Chem. Eur. J. 2016, 15, 5156-5159. [LINK]

Picture2

  • Wiberg, K. B.; Lambert, K. M.; BAILEY, W. F.; The Role of CH···O Coulombic Interactions in Determining Rotameric Conformations of Phenyl Substituted 1,3-Dioxanes and Tetrahydropyrans. J. Org. Chem. 201580, 7884-7889. [LINK]

Picture1

  • BAILEY, W. F.; Lambert, K. M.; Wiberg, K. B.; Mercado, B. Q. Effect of Remote Aryl Substituents on the Conformational Equilibria of 2,2,-Diaryl-1,3-dioxanes: Importance of Electrostatic Interactions. J. Org. Chem. 2015, 80, 4108-4115. [LINK]

Angew2015

  • Kelly, C. B.; Lambert, K. M.; Mercadante, M. A.; Ovian, J. M.; BAILEY, W. F.; Leadbeater, N. E. Access to Nitriles from Aldehydes Mediated by an Oxoammonium Salt.  Angew. Chem. Int. Ed. 2015, 54, 4241-4245. [LINK]tetletters2015
  • Wiberg, K. B.; Lambert, K. M.; BAILEY, W. F. Rotamers of Phenyl Substituted 1,3-Dioxanes and Tetrahydropyrans: Importance of CH…O Coulombic Interactions. Tetrahedron Lett. 2015, 56, 3438–3440. [LINK]orgletters2014.6484.
  • Lambert, K. M.; Bobbitt, J. M; Eldirany, S. A.; Wiberg, K. B; BAILEY, W. F. Facile Oxidation of Primary Amines to Nitriles Using an Oxoammonium Salt. Org. Lett. 2014, 16, 6484-6487.  [LINK ]

10722

  • Luderer, M. R.; Mealy, M. J.; BAILEY, W. F. Asymmetric Intramolecular Carbolithiation of Achiral Substrates: Synthesis of Enantioenriched (R)-(+)-Cuparene and (R)-(+)- Herbertene. J. Org. Chem. 2014, 79, 10722-10726. [LINK]

tetrahedron.2014.4807

  • BAILEY, W. F.; Wiberg, K. B.; Bartelson, A. L. Reactions of Adamantanethione with Grignard Reagents: There is no Evidence of Addition to the C=S Bond. Tetrahedron Lett. 2014, 55, 4807-4809. [LINK]

1055

  • Bobbitt, J. M.; Bartelson, A. L.; BAILEY, W. F.; Hamlin, T. A.; Kelly, C. B. Oxoammonium Oxidations of Alcohols in the Presence of Pyridine Bases. J. Org. Chem. 2014, 79, 1055-1076.  [LINK]

J. Org. Chem. 2013, 78, 3493

  • BAILEY, W. F.; Bakonyi, J. M. Intramolecular Carbolithiation as a Route to a Sterically Congested Cyclopentene: Synthesis of the Longtailed Mealybug Pheromone. J. Org. Chem. 2013, 78, 3493-3495.  [LINK]

Beil. J. Org. Chem. 2013, 9, 537

  • BAILEY, W. F.; Fair, J. D. Intramolecular Carbolithiation Cascades as a Route to a Highly Strained Carbocyclic Framework: Competition between 5-Exo-Trig Ring Closure and Proton Transfer. Beil. J. Org. Chem. 2013, 9, 537-543. [LINK]

J. Org. Chem. 2013, 73, 1742

  • Wiberg, K. B.; BAILEY, W. F. A Computational Study of the Enantioselective Deprotonation of a Cyclopropanecarboxamide with an Alkyllithium in the Presence of Sparteine. J. Org. Chem. 2013, 78, 1742-1746. [LINK]

J. Am. Chem. Soc. 2012, 134, 3199

  • BAILEY, W. F.; Bartelson, A. L;.; Wiberg, K. B. Contrasting Reactions of Ketones and Thioketones with Alkyllithiums: A Coordinated Experimental and Computational Investigation J. Am. Chem. Soc. 2012, 134, 3199 – 3207. [LINK]

org.letters.2012.14.350

  • Qiu, J. C.; Pradhan, P. P.; Blanck, N. B.; Bobbitt, J. M.; BAILEY, W. F. Selective Oxoammonium Salt Oxidations of Alcohols to Aldehydes and Aldehydes to Carboxylic Acids. Org. Lett. 2012, 14, 350 – 353. [LINK]

jphyschemA.2011.115.12624

  • Wiberg, K. B.; BAILEY, W.F.; Petersson, G. A. A Computational Study of the Properties and Reactions of Small Molecules Containing O, S and Se. J. Phys. Chem. A 2011, 115, 12624 – 12630. [LINK]

 

  • Wiberg, K. B.; Bartelson, A. L.; BAILEY, W. F. Disparate Behavior of Ketones and Thioketones on Reaction with Organolithiums. Tetrahedron Lett. 2011, 52, 2169-2171. [LINK]

 

  • Fair, J. D.; BAILEY, W.F.; Felty, R. A.; Gifford, A. E.; Shultes, B.; Volles, L. H. Quantitation by Portable Gas Chromatography – Mass Spectrometry of VOCs Associated with Vapor Intrusion. Int. J. Anal. Chem. 2010, Article ID 278078, 6 pages, 2010. doi:10.1155/2010/278078 [LINK]

. Org. Chem. 2010, 75, 2661

  • BAILEY, W.F.; Luderer, M.R.; Uccello, D.P.; Bartelson, A.L. Effect of Solvent and Temperature on the Lithium-Bromine Exchange of Vinyl Bromides: Reaction of n-Butyllithium and t-Butyllithium with (E)-5-Bromo-5-decene. J. Org. Chem. 2010, 75, 2661-2666. [LINK ]

 

  • BAILEY, W.F.; Luderer, M.R. Asymmetric Addition of Chiral Methylmagnesium Alkoxides to Benzaldehyde. Arkivoc, 2010, part viii, 108-115. [LINK ]

jorgchem.2009.74.9524

  • Pradhan, P.P.; Bobbitt, J.M.; BAILEY, W.F. Oxidative Cleavage of Benzylic and Related Ethers Using Oxoammonium Salt. J. Org. Chem. 2009, 74, 9524-9527.  [LINK ]

 

  • BAILEY, W.F.; Ovaska, T.V. Allylic Proton – Proton Coupling in Stereodefined Alkylidenecyclobutanes and Alkylidenecyclopentanes. J. Mex. Chem. Soc. 2009, 53, 139-142.  [LINK ]

jorgchem3659

  • Wiberg, K. B.; Wang, Y.; Miller, S. J.; Puchlopek, A. L.; BAILEY, W. F.; Fair, J. D. Disparate Behavior of Carbonyl and Thiocarbonyl Compounds: Acyl Chlorides vs Thiocarbonyl Chlorides and Isocyanates vs Isothiocyanates. J. Org. Chem. 2009, 74, 3659-3664. [LINK ]

tetrahedron assymetry2009.981

  • Luderer, M. R.; BAILEY, W. F.; Luderer, M. R.; Fair, J. D.; Dancer, R. J.; Sommer, M. B. Asymmetric Addition of Achiral Organomagnesium Reagents or Organolithiums to Achiral Aldehydes or Ketones: A Review. Tetrahedron: Asymmetry 2009, 20, 981 – 998. [LINK ]

org.processres.dev.2009.13.144

  • Rathman, T. L.; BAILEY, W. F. Optimization of Organolithium Reactions. Org. Process Res. Dev. 2009, 13, 144-151. [LINK ]

jchemtheorycomput.2009.5.1033

  • Wiberg, K. B.; Wang, Y.; Petersson, G. A.; BAILEY, W. F. Intramolecular Non-bonded Attractive Interactions: 1-Substituted Propenes. J. Chem. Theory Comput. 2009, 5, 1033-1037. [LINK]

orgletters2008.10.1071

  • BAILEY, W. F.; Salgaonkar, P. D.; Brubaker, J. D.; Sharma, V. Preparation of the Isomeric Azaindoline Family by Intramolecular Carbolithiation. Org. Lett. 2008, 10, 1071-1074.  [LINK ]

 

  • BAILEY, W. F.; Rathman, T. L. The Lithium–Halogen Exchange Reaction in Process Chemistry. In “Process Chemistry in the Pharmaceutical Industry: Challenges in an Ever Changing Climate”, Vol. 2; Gadamasetti, K. and Braish, T., Eds.; CRC Press: Boca Raton, FL; 2008; Chapter 12, p. 205-216.

orgletters2007.4504

  • BAILEY, W. F.; Bobbitt, J. M.; Wiberg, K. B. Mechanism of the Oxidation of Alcohols by Oxoammonium Cations. J. Org. Chem. 2007, 72, 4504-4509. [LINK ]

orglttrs2006.8.5485

  • Pradhan, P. P.; Bobbitt, J. M.; BAILEY, W. F.  Ene-Like Addition of an Oxoammonium Cation to Alkenes: Highly Selective Route to Allylic Alkoxyamines. Org. Lett. 2006, 8, 5485-5487.  [LINK ]

 

  • BAILEY, W. F. Asymmetric Cyclization of Achiral Organolithiums. J. Mex. Chem. Soc. 2006, 50, 81. [LINK ]

 

  • BAILEY, W. F. t-Butyllithium – An Update. In “Electronic Encyclopedia of Reagents for Organic Synthesis”, Paquette, L. A., Ed.; Wiley: New York, NY, 2006.

jorgchm2000652014

  • BAILEY, W. F.; Luderer, M. R.; Jordan, K. P. Effect of Solvent on the Lithium-Bromine Exchange of Aryl Bromides:  Reactions of n -Butyllithium and t -Butyllithium with 1-Bromo-4- t -butylbenzene at 0 °C.  J. Org. Chem. 2006, 7 , 2825-2828. [LINK ]

 

  •  BAILEY, W. F.; Jiang, X. Stereochemistry of the Cyclization of 4-( t -Butyldimethyl)siloxy-5-hexenyllithium: cis -Selelective Ring-Closure Accompanied by Retro-[1,4]-Brook Rearrangement.  Arkivoc, 2005 , Part iv, 25-32. [LINK]

tetrahedron letters 2005

  • BAILEY, W. F.; Jiang, X. Stereochemistry of the Cyclization of Alkoxy-Substituted 5-Hexenyllithiums: Effect of Solvent and Lithium Iodide on Diastereoselectivity. Tetrahedron 2005, 61, 3183-3794. [LINK ]

 

jamchmsoc2002,2004,1889,1540

  • O’Brien, P.; Wiberg, K. B.; BAILEY, W. F.; Hermet, J-P. R.; McGrath, M. J. An Experimental and Computational Study of the Enantioselective Lithiation of N -Boc Pyrrolidine Using Sparteine-like Chiral Diamines. J. Am. Chem. Soc. 2004, 126, 15480-15489. [LINK ]

 

  • BAILEY, W. F.; Luderer, M. R.; Mealy, M. J.; Punzalan, E. R. Generation and Cyclization of 5-Hexenyllithium: Preparation of 2-Cyclopentylacetophenone. Organic Syntheses 2004, 81, 121-133. [LINK ]

 

  • Mealy, M. J.; Luderer, M. R.; BAILEY, W. F.; Sommer, M. B. Effect of Ligand Structure on the Asymmetric Cyclization of Achiral Olefinic Organolithiums. J. Org. Chem. 2004, 69, 6042-6049. [LINK ]

jorgchm2000652014

  • BAILEY, W. F., Brubaker, J. D., Jordan, K. P. Effect of Solvent and Temperature on the Lithium–Iodine Exchange of Primary Alkyl Iodides: Reaction of t -Butyllithium with 1-Iodooctane in Heptane–Ether Mixtures. J. Organomet. Chem. 2003, 681, 210-214. [LINK ]

jamchmsociety2000.122.6787

  • BAILEY, W. F.; Luderer, M. R.; Mealy, M. J. Preparation of Differentially 1,3-Disubstituted Indolines by Intramolecular Carbolithiation. Tetrahedron Lett. 2003, 44, 5303-5305. [ LINK]

jorgchem681334

  • BAILEY, W. F.; Daskapan, T.; Rampalli, S. Cyclization of Aryllithiums Tethered to Methylenecycloalkanes: Stereoselective Synthesis of 4 a -Substituted cis-Hexahydrofluorenes. J. Org. Chem. 2003, 68, 1334-1338. [LINK ]

Angew 2000

  • Wiberg, K. B.; BAILEY, W. F. Dipole-Stabilized Carbanions: A Computational Study of N-Methylformamide Anion and Methyl N -Methylcarbamate Anion. J. Org. Chem. 2002, 67, 5365-5368. [LINK ]

LEtters 2002, 4,791

  • BAILEY, W. F.; Mealy, M. J.; Wiberg, K. B Comparative Study of Anionic and Radical Cyclization for the Preparation of 1,3-Dimethylindans: Highly Stereoselective Preparation of cis -1,3-Disubstituted Indans via Intramolecular Carbolithiation. Org. Lett. 2002, 4, 791-794.  [LINK ]

jamchmsoc2002,2004,1889,1540

  • BAILEY, W. F.; Beak, P.; Kerrick, S. T.; Ma, S.; Wiberg, K. B. An Experimental and Computational Investigation of the Enantioselective Deprotonation of Boc-Piperidine. J. Am. Chem. Soc. 2002, 124, 1889-1896. [LINK ]

 

  • Mealy, M. J.; BAILEY, W. F. Synthesis of Heterocycles by Cyclization of Unsaturated Organolithiums: A Review. J. Organomet. Chem. 2002, 646, 59-67. [LINK ]

 

  • BAILEY, W. F.; Zarcone, L. M. J. Regioselective and Stereoselective Cleavage of cis -4-Methyl-2-vinyl-1,3-dioxane by Alkyllithiums. Chirality. 2002, 14, 163-165. [LINK]

 

  • BAILEY, W. F.; Longstaff, S. C. Cyclization of Methyl-Substituted 6-Heptenyl Radicals. Org. Lett. 2001, 3, 2217-2219. [LINK ]

lettters 3 1865

  • BAILEY, W. F.; Reed, D. P.; Clark, D. R.; Kapur, G. N. Grignard Reactions of 4-Substituted-2-keto-1,3-dioxanes: Highly Diastereoselective Additions Controlled by a Remote Alkyl Group. Org. Lett. 2001, 3, 1865-1868. [LINK ]

Angew 2000

  • Wiberg, K. B.; BAILEY, W. F. Chiral Diamines 4. A Computational Study of the Enantioselective Deprotonation of Boc-Pyrrolidine with an Alkyllithium in the Presence of a Chiral Diamine. J. Am. Chem. Soc. 2001, 123, 8231-8238. [LINK ]

 

  • BAILEY, W. F.; Longstaff, S. C. “tert-Butyllithium in Organic Synthesis: a Brief Review. Part 2.” Chimica Oggi (Chemistry Today) 2001, 19(3-4), 28-32.

 

  • BAILEY, W. F.; Longstaff, S. C. “tert-Butyllithium in Organic Synthesis: a Brief Review. Part 1.” Chimica Oggi (Chemistry Today) 2001, 19(1-2), 27-31.

jorgchm2000652014

  • Wiberg, K. B.; Sklenak, S.; BAILEY, W. F. A Computational Study of 10-X-2 Ate Complexes Derived from Vinyllithiums and Vinyl Halides. Organometallics 2001, 20, 771-774. [LINK ]

 

  • Wiberg, K. B.; BAILEY, W. F. Chiral Diamines. 1. Relative Energies of (–)-Sparteine Conformers, Interconversion Barriers, and Alkyllithum Complexes. J. Mol. Struct. 2000, 556, 239-244. [LINK ]

 

  • BAILEY, W. F.; Longstaff, S. C. tert-Butyllithium in Organic Synthesis. “Lithium Link”; FMC Corporation: Gastonia, NC, 2000, p. 1-11.

Angew 2000

  • Wiberg, K. B.; BAILEY, W. F. Chiral Diamines 3. Effect of Ligand Structure on the Enantioselective Deprotonation of N -Boc-pyrrolidine with i -PrLi: a Computational Comparison of (–)-Sparteine and (S,S)-1,2-Bis( N , N -dimethylamino)cyclohexane. Tetrahedron Lett. 2000, 41, 9365-9368. [LINK ]
  • Wiberg, K. B.; BAILEY, W. F. A Transition State for the Enantioselective Deprotonation of N -Boc-pyrrolidine with Isopropyllithium–(–)-Sparteine. Angew. Chem. Int. Ed. 2000, 39, 2127-2129. [LINK ]

jamchmsociety2000.122.6787

  • BAILEY, W. F.; Mealy, M. J. Asymmetric Cyclization of Achiral Olefinic Organolithiums Controlled by a Stereogenic Lithium: Intramolecular Carbolithiation in the Presence of (–)-Sparteine. J. Am. Chem. Soc. 2000, 122, 6787-6788. [LINK ]

jorgchm2000652014

  • Wiberg, K. B.; Sklenak, S.; BAILEY, W. F. Solvation and Structural Effects on the Stability of 10-X-2 Ate Complexes: a Computational Study. J. Org. Chem. 2000, 65, 2014-2021. [LINK ]

2000 65 1181

  • Wiberg, K. B.; Castejon, H.; BAILEY, W. F.; Ochterski, J. Conformational Studies in the Cyclohexane Series. 2. Phenylcyclohexane and 1-Methyl-1-phenylcyclohexane. J. Org. Chem. 2000, 65 , 1181-1187. [LINK ]

 

  • BAILEY, W. F.; England, M. E.; Mealy, M. J.; Thongsornkleeb, C.; Teng, L. Facile O-Deallylation of Allyl Ethers via S N 2′ Reaction with tert-Butyllithium. Org. Lett. 2000, 2, 489-491.  [LINK ]