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William F Bailey

Explore the profile of William F Bailey including associated specialties, affiliations and a list of published articles. Areas
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Recent Articles
1.
Bobbitt J, Eddy N, Bruckner C, Bailey W, Merbouh N
J Org Chem . 2023 Feb; 88(5):3321-3325. PMID: 36812364
Propargyl alcohol derivatives were readily oxidized using Bobbitt's salt to yield the corresponding propynal products. 2-Butyn-1,4-diol may be selectively oxidized to provide either 4-hydroxy-2-butynal or acetylene dicarboxaldehyde, and the resulting...
2.
Wiberg K, Bailey W, Lambert K
J Org Chem . 2019 Apr; 84(9):5783-5789. PMID: 30933498
In order to elucidate to what extent Coulombic and other interactions contribute to the origins of contrasteric phenomena, we have identified a significant, previously unrecognized interaction between fluorine-containing motifs and...
3.
Wiberg K, Bailey W, Lambert K, Stempel Z
J Org Chem . 2018 Apr; 83(9):5242-5255. PMID: 29620891
The origin of the anomeric effect has been reexamined in a coordinated experimental and computational investigation. The results of these studies implicate a number of different, but correlated, interactions that...
4.
Lambert K, Stempel Z, Wiberg K, Bailey W
Org Lett . 2017 Nov; 19(23):6408-6411. PMID: 29144141
Base-catalyzed equilibration of anancomeric cyanocyclohexanes demonstrates that replacement of cis-3,5-dimethyl holding groups with electron-withdrawing CF groups dramatically increases the proportion of the axial cyano isomer present at equilibrium. The CF...
5.
Lambert K, Stempel Z, Kiendzior S, Bartelson A, Bailey W
J Org Chem . 2017 Oct; 82(21):11440-11446. PMID: 28968489
The multigram preparation and characterization of a novel TEMPO-based oxoammonium salt, 2,2,6,6-tetramethyl-4-(2,2,2-trifluoroacetamido)-1-oxopiperidinium tetrafluoroborate (5), and its corresponding nitroxide (4) are reported. The solubility profile of 5 in solvents commonly used...
6.
Bailey W, Lambert K, Stempel Z, Wiberg K, Mercado B
J Org Chem . 2016 Dec; 81(24):12116-12127. PMID: 27978750
Anancomeric 5-phenyl-1,3-dioxanes provide a unique opportunity to study factors that control conformation. Whereas one might expect an axial phenyl group at C(5) of 1,3-dioxane to adopt a conformation similar to...
7.
Bailey W, Fair J
J Org Chem . 2016 Apr; 81(9):3951-5. PMID: 27074433
Lithium-iodine exchange-initiated fragmentation of a series of 4-substituted 2-iodomethyl-1,3-dioxanes proceeds rapidly and regioselectively to afford enol ether alcohols by preferential cleavage of the less congested C(2)-O(1) bond. The results demonstrate...
8.
Lambert K, Bobbitt J, Eldirany S, Kissane L, Sheridan R, Stempel Z, et al.
Chemistry . 2016 Feb; 22(15):5156-9. PMID: 26868873
Synergism among several intertwined catalytic cycles allows for selective, room temperature oxidation of primary amines to the corresponding nitriles in 85-98% isolated yield. This metal-free, scalable, operationally simple method employs...
9.
Wiberg K, Wang Y, Petersson G, Bailey W
J Chem Theory Comput . 2015 Nov; 5(4):1033-7. PMID: 26609612
Whereas cis-substituted alkenes are normally significantly less stable than the trans-isomers, there is a group of 1-substituted propenes (X = F, OMe, Cl, Br, SMe) where the cis-isomers are the...
10.
Wiberg K, Lambert K, Bailey W
J Org Chem . 2015 Jul; 80(16):7884-9. PMID: 26182246
The rotameric conformations of the phenyl ring in both the axial and the equatorial conformers of phenyl substituted 1,3-dioxanes and tetrahydropyrans are compared with those of the corresponding phenylcyclohexanes at...