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Recent Publications 1995 -2006

•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 , 71 , 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 ]

•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 ]

•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 ]

•  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 ]

•  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 ]

•  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 ]

•  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 ]

•  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 . Letters 2002 , 4 , 791 - 794. [ LINK ]

•  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 . Letters 2001 , 3 , 2217 - 2219. [ LINK ]

•  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. Letters 2001 , 3 , 1865 - 1868. [ LINK ]

•  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.

•  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.

•  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. Engl . 2000 , 39 , 2127 - 2129. [ LINK ]

•  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 ]

•  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 ]

•  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. Letters 2000 , 2 , 489 - 491. [ LINK ]

•  BAILEY, W. F.; Longstaff, S. C. Cyclization of Benzyne–Tethered Alkyllithiums: Preparation of 3-Substituted Benzocyclobutenes and 5-Substituted Tetralins. Tetrahedron Lett. 1999 , 40 , , 6899 - 6901. [ LINK ]

•  BAILEY, W. F.; Carson, M. W. PhLi–Initiated Cycloisomerization of Unsaturated Organoiodides: Mechanism of the Isomerization of Olefinic Primary Alkyl Iodides. Tetrahedron Lett. 1999 , 40 , 5433 - 5437. [ LINK ]

•  Wiberg, K. B.; Hammer, J. D.; Castejon, H.; BAILEY, W. F.; DeLeon, E. L.; Jarret, R. M. Conformational Studies in the Cyclohexane Series. 1 Experimental and Computational Investigation of Methyl, Ethyl, Isopropyl and t -Butylcyclohexanes. J. Org. Chem. 1999 , 64 , 2085 - 2095. [ LINK ]

•  BAILEY, W. F.; Carson, M. W. Catalytic Cycloisomerization of Unsaturated Organoiodides. J. Org. Chem. 1998 , 63 , 9960 - 9967. [ LINK ]

•  Cioffi, E. A.; BAILEY, W. F. Facile Preparation of Pyrylium and Pyridinium Bromides Under Neutral Conditions. Tetrahedron Lett. 1998 , 39, 2679 - 2680. [ LINK ]

•  BAILEY, W. F.; Longstaff, S. C. Generation and Cyclization of a Benzyne–Tethered Alkyllithium: Preparation of 4-Substituted Indans. J. Org. Chem. 1998 , 63 , 432 - 433. [ LINK ]

•  BAILEY, W. F.; Carson, M. W. Lithium–Iodine Exchange Mediated Atom Transfer Cyclization: Catalytic Cycloisomerization of 6-Iodo-1-hexene. J. Org. Chem. 1998 , 63 , 361 - 365. [ LINK ]

•  Bett, J. S.; Kunz, H. R.; Aldykiewicz, A. J., Jr.; Fenton, J.; BAILEY, W.F.; McGrath, D. V. Platinum – Macrocycle Co-catalysts for the Electrochemical Oxidation of Methanol. Electrochim. Acta 1998 , 43 , 3645 - 3655. [ LINK ]

•  BAILEY, W. F.; Tao, Y. Efficient Preparation of Vinylcyclopropane by S N ' Cyclization of the Organolithium Derived from (E)-5-Iodo-1-methoxy-2-pentene. Tetrahedron Lett. 1997 , 38 , 6157 - 6158. [ LINK ]

•  BAILEY, W. F.; Croteau,A. A.; Rivera, A. D. The Stereochemistry of the Grignard – Ortho Ester Reaction Revisited: Regioselective Endocyclic Cleavage in the Reaction of Grignard Reagents with cis -2-Methoxy-4-methyl-1,3-dioxane. Tetrahedron Lett. 1997 , 38 , 4047 - 4050. [ LINK ]

•  BAILEY, W. F.; Carson, M. W.; Zarcone, L. M. J. Selective Protection of 1,3-Diols at the More Hindered Hydroxyl Group: 3-(Methoxymethoxy)-1-butanol. Organic Syntheses 1997 , Vol. 75, p. 177-183.

•  BAILEY, W. F.; Carson, M. W. Reaction of Organolithiums with Fluoro-N,N-diallylanilines: A Benzyne–Mediated Anionic Cascade Leading to 3,4-Disubstituted Indolines. Tetrahedron Lett. 1997 , 38 , 1329 - 1332. [ LINK ]

•  BAILEY, W. F.; Wachter-Jurcsak, N. M.; Pineau, M. R.; Ovaska, T. V.; Warren, R. R.; Lewis, C. E. Acetylenic Vinyllithiums: Consecutive Cycloisomerization – [4+2] Cycloaddition Reactions. J. Org. Chem. 1996 , 61 , 8216 - 8228. [ LINK ]

•  BAILEY, W. F.; Punzalan, E. R. Isomerization of 2-(2-Propenoxy)phenyllithium: Tandem Anionic Cyclization – g -Elimination. Tetrahedron Lett. 1996 , 37 , 5435 - 5436. [ LINK ]

•  BAILEY, W. F. Review of “Modern Conformational Analysis: Elucidating Novel Exciting Molecular Structures” by Helena Dodziuk; VCH Publishers, Inc.: New York, 1995. J. Med Chem. 1996 , 39 , 1754.

•  BAILEY, W. F.; Jiang, X.-L. Preparation of Substituted Indolines via Anionic Cyclization. J. Org. Chem. 1996 , 61 , 2596 - 2597. [ LINK ]

•  BAILEY, W. F.; Jiang, X.-L.; McLeod, C. E. Conformational Control in the Cyclization of an Unsaturated Vinyllithium: Synthesis of (±)-Laurene. J. Org. Chem. 1995 , 60 , 7791-7795.

•  Jiang, X-L.; BAILEY, W. F. Facile Retro-[1,4]-Brook Rearrangement of a [(2-Siloxy­cyclopentyl)methyl]lithium Species . Organometallics 1995 , 14 , 5704 - 5707.

•  BAILEY, W. F.; Zarcone, L. M. J.; Rivera, A. D. Selective Protection of 1,2- and 1,3-Diols via Acylative Cleavage of Cyclic Formals. J. Org. Chem. 1995 , 60 , 2532-2536.

•  BAILEY, W. F.; Wachter-Jurcsak, N. t -Butyllithium. In “Encyclopedia of Reagents for Organic Synthesis”, Paquette, L. A., Ed.; Wiley: New York, NY, 1995 , p. 914 - 920.

•  BAILEY, W. F.; Punzalan, E. R.; Della, E. W.; Taylor, D. K. Ring-Opening of (Cyclobutylmethyl)lithium and [(3- tert -Butyl-1-bicyclo[1.1.1]pentyl)methyl]lithium. J. Org. Chem. 1995 , 60 , 297-300.

•  BAILEY, W. F.: Aspris, P. H. Facile Preparation of Alkenylidenecycloalkanes by Cyclization of Acetylenic Alkyllithiums Bearing a Propargylic Leaving Group. J. Org. Chem. 1995 , 60 , 754-757.

 

William F. Bailey

Department of Chemistry,  Unit 3060
55 North Eagleville Rd
University of Connecticut
Storrs, CT.  06269-3060

Phone: 860-486-2163
Email: william.bailey@uconn.edu

 

 

 

 
      
  UCONN Chemistry Department, Unit 3060
55 North Eagleville Rd.
University of Connecticut
Storrs, CT 06269
Phone: (860)-486-2012
Fax: (860)-486-2981