Development of new synthetic methodology using main-group organometallic chemistry. Investigation of the synthetic utility of unsaturated organolithiums and related Group 1 organo?metallics. These reactive intermediates, prepared in virtually quantitative yield by low-temperature lithium-iodine exchange between t-butyllithium and an organoiodide, undergo regiospecific and highly stereoselective cyclization upon warming. The high degree of stereocontrol in these anionic cyclizations has led to development of one step, stereoselective syntheses of simple natural products and tandem-cyclization strategies for the preparation of bi- and polycyclic structures.

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 ]

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 ]

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 ]

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 ]

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. Letters 2012, 14, 350 - 353. [ LINK ]

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 ]

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 ]

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 ]

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 ]

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 ]

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

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 ]

BAILEY, W. F.; Salgaonkar, P. D.; Brubaker, J. D.; Sharma, V. Preparation of the Isomeric Azaindoline Family by Intramolecular Carbolithiation. Org. Letters 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.

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 ]

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. Letters 2006, 8, 5485 – 5487. [ LINK ]