Book Contributions
“Hydrogen Bromide” Breton, G. W.; Kropp, P. J. in the Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A.,Ed.; Wiley: New York, 1995, p 2704.
“Hydrogen Chloride” Breton, G. W.; Kropp, P. J. in the Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A., Ed.; Wiley: New York, 1995, p 2707.
“Hydrogen Iodide” Breton, G. W.; Kropp, P. J.; Harvey, R. G. in the Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A., Ed.; Wiley: New York, 1995, p 2728.
“Hydrazoic Acid” Breton, G. W.; Kropp, P. J. in the Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A., Ed.; Wiley: New York, 1995, p 2685
Scholarly Research Articles
"Spontaneous elimination of halides from β-halo carbanions upon geometry optimizations: Computational predictions of the outcomes from elimination reactions proceeding via an E1cb-Like mechanism" Breton, G.W. Computational and Theoretical Chemistry 2023, 1227, 114257. https://doi.org/10.1016/j.comptc.2023.114257
"An Unexpected Change in Reaction Mechanism in the homo-Diels-Alder Cycloadditions of N-Methyl-1,2,4-triazoline-3,5-dione with a series of Bicycloalkadienes" Breton, G.W. Journal of Physical Organic Chemistry 2023, 36, e4513. https://doi.org/10.1002/poc.4513
[Selected for issue cover]
"Evaluating the Effectiveness of Tethered Bis(urazolyl) Diradicals as Molecular Building Blocks for Dynamic Covalent Chemistry" Breton, G.W.; Martin, K.L.; Bowron, J.A.; Bacsa, J. Journal of Organic Chemistry 2023, 88, 9157-9166. https://doi.org/10.1021/acs.joc.3c00732
"Computational Modeling of the Feasibility of Substituted [1.1.1]Propellane Formation from Anionic Bridgehead Bromide Precursors" Gates, K.E., Herring, C., Lumpkin, A.T., Maraski, R.J., Perry, E.G., Prado, M.G., Quigley, S.L., Ridlehoover, J.V., Salazar, E., Sims, K., Stephenson, K.R., Stewart, E.A., Sullivan, M.E., Tucker, J.R., Breton, G.W. Organics 2023, 4, 196-205. https://doi.org/10.3390/org4020016
"Reinvestigation of the Room Temperature Photochemical Reaction between N-Methyl-1,2,4-triazoline-3,5-dione (MeTAD) and Benzene" Breton, G. W. Organics 2023, 4, 164-172. https://doi.org/10.3390/org4020013
[Invited manuscript for the special issue "Chemistry of Heterocycles"]
"Exploring the Limits of Reactivity of N-Methyl-1,2,4-triazoline-3,5-dione (MeTAD) with Disubstituted Bicycloalkadienes in the Homo-Diels–Alder Reaction" Breton, G. W.; Martin, K. L. Organics, 2023, 4, 41-48. https://doi.org/10.3390/org4010002.
[Invited manuscript for the special issue "Advanced Research Papers in Organics"]
[Selected for Issue Cover]
"1-(4-{[3,5-bis({[3,5-Dimethyl-4-(4-methyl-3,5-dioxo-1,2,4-triazolidin-1-yl)-phenoxy]methyl})phenyl]methoxy}-2,6-dimethyl-phenyl)-4-methyl-1,2,4-triazolidine-3,5-dione" Breton, G.W.; Bowron, J.A., Jr. Molbank 2023, 2023, M1535. https://doi.org/10.3390/M1535
[Invited manuscript for the special issue "Heterocycle Reactions"]
1-[2,6-Dimethyl-4-(pent-4-yn-1-yloxy)phenyl]-4-phenyl-1,2,4-triazolidine-3,5-dione" Breton, G. W. Molbank 2023, 2023, M1578.
[Invited manuscript for the special issue "Structure Determination"]
[Selected to be highlighed on homepage of Molbank]
"Efficient Routs for the Preparation of Urazole Radical Self-Assembled Monolayers on Gold Surfaces" Campos-Lendinez, A.; Crivellers, N.; Bromley, S. T.; Rovira, C. Breton, G. W.; Mas-Torrent, M. Journal of Physical Chemistry C 2022, 126, 13358-13365. https://doi.org/10.1021/acs.jpcc.2c02453.
"Competition between the stabilizing effects of saturated alkyl substituents and pi bonds on complexes of silver ion (Ag+) with alkenes" Breton, G. W. Journal of Physical Organic Chemistry 2021. https://doi.org/10.1002/poc.4301
[Selected for Issue Cover]
"Probing the Dynamic Covalent Chemistry Behavior of Nitrogen-Centered Di- and Triurazole Radicals" Breton, G. W.; Martin, K. L. Journal of Organic Chemistry 2020, 15, 10865-10871. https://doi.org/10.1021/acs.joc.0c01425
"Structural Consequences of the 1,2,3‐Triazole as an Amide Bioisostere in Analogues of the Cystic Fibrosis Drugs VX‐809 and VX‐770" Doiron, J. E.; Le, C. A.; Bacsa, J.; Breton, G. W.; Martin, K. L.; Aller, G. A; Turlington, M. Chem Med Chem 2020, 15, 1720-1730. https://doi.org/10.1002/cmdc.202000220
"Structural Verification of a tetrahydrotetrazole compound" Breton, G. W.; Hahn, L. A.; Martin, K. L. Acta Crystallographica Section C 2019, C75. https://doi.org/10.1107/S2053229619010210
"A Search for X-ray Crystallographic Evidence of n-> pi* Interactions in a Series of Substituted 2-(Dimethylamino)biphenyl-2'-carboxaldehydes" Breton, G. W.; Davis, L. O.; Martin, K. L.; Chambers T. A. Crystal Growth & Design 2019, 19, 3895–3904. https://doi.org/10.1021/acs.cgd.9b00322
"Evaluation of 1,2,3-Triazoles as Amide Bioisosteres in Cystic Fibrosis Transmembrane Conductance Regulator Modulators VX-770 and VX-809" Doiron, J. E.; Le, C. A.; Ody, B. K.; Brace, J. B.; Post, S. J. Thacker, N. L.; Hill, H. M.; Breton, G. W.; Mulder, M. J.; Chang, C.; Bridges, T. M.; Tang, L.; Wang, W.; Rowe, S. M.; Aller, S. G.; Turlington, M. Chem. Eur. J, 2019, 25, 3362-3674. https://doi.org/10.1002/chem.201805919
"Factors affecting the dimerization of persistent nitrogen-centered 1-phenyl urazole radicals to tetrazanes" Breton, G. W. Journal of Physical Organic Chemistry, 2018, 31:e3808.
"DFT study of ortho, meta and para-pyridyl cations. Pyridynium found?" Breton, G. W. Computational and Theoretical Chemistry 2018, 1173, 51-57.
"Unanticipated formation of a novel octaazacyclodecane ring upon oxidation of a 1,1,-bis-urazole" Breton, G. W.; Martin, K. L. Acta Crystallographica Section C 2018, C74, 558-563.
"Computational, 1H NMR, and X-ray structural studies on 1-arylurazole tetrazane dimers" Martin, K. L.; Breton, G. W. Acta Crystallographica Section C 2017, C73, 660-666.
“An ab initio Study of the Effect of Substituents on the n-> pi* Interactions between 7-Azaindole and 2,6-Difluorosubstituted Pyridines” Singh, S. K.; Das, A.; Breton, G. W. Journal of Physical Chemistry A, 2016, 6258-6269.
“Intermediacy of Persistent Urazole Radical and an Electrophilic Diazenium Species in the Acid-Catalyzed Reaction of MeTAD with Anisole” Breton, G. W.; Suroviec, A. H. Journal of Organic Chemistry, 2016, 81, 206-214.
“Substituted 2-(Dimethylamino)biphenyl-2′-carboxaldehydes as Substrates for Studying n→π Bürgi–Dunitz Trajectory” Breton, G. W.; Crasto, C. J. Journal of Organic Chemistry, 2015, 80, 7375-7384.
“Unexpected Sigma Bond Rupture during the Reaction of N-Methyl-1,2,4- triazoline-3,5-dione with Acenaphthylene and Indene” Breton, G. W.; Hughes, J. S.; Pitchko, T. J.; Martin, K. M.; Hardcastle, K. Journal of Organic Chemistry, 2014, 79, 8212-8220.
“Alternative Synthetic Routes to N-Methyl-1,2,4-triazoline-3,5-dione (MeTAD) and other Triazolinedione derivatives” Breton, G. W.; Turlington, M. Tetrahedron Letters 2014, 55, 4661-4663.
“Convenient Synthesis of Monobenzylated Hydrazides via Aqueous Zinc-Mediated Addition Reactions” Breton, G. W. Synthetic Communications, 2014, 44, 1128-1136.
“Application of Radical Cation Spin Density Maps toward the Prediction of Photochemical Reactivity between N-Methyl-1,2,4-triazoline-3,5-dione and Substituted Benzenes” Breton, G. W.; Hoke, K. R. Journal of Organic Chemistry, 2013, 78, 4697-4707.
“Acid-Catalyzed Reactions of N-Methyl-1,2,4-Triazoline-3,5-Dione (MeTAD) with Some Polyaromatic Hydrocarbons” Breton, G. W. Advanced Chemistry Letters, 2013,1, 68-73.
“Synthesis of Monoaryl Hydrazides via the BF3 Catalyzed Reaction of Diethyl Azodicarboxylate with Substituted Benzenes” Breton, G. W.; Grigalunas, M. J.; Hughes, J. S. American Journal of Organic Chemistry, 2012, 26, 132-135.
“One-Pot Synthesis of Novel 2,3-Dihydro-1H-indazoles” Breton, G. W.; Lepore, A. J.
Molecules, 2011, 16, 9553-9561.
“Acid•Catalyzed Reaction of 4-Methyl-1,2,4-triazoline-3,5-dione (MeTAD) with Substituted Benzenes” Breton, G. W. Tetrahedron Letters, 2011, 52, 733-735.
“Thermal Decomposition of meso- and d,l-3,4-diethyl-3,4-dimethyldiazetine-N,N'-dioxide” Breton, G. W.; Nickerson, J. E.; Greene, A. M.; Oliver, L. H. Organic Letters 2007, 9, 3005-3008.
“Synthesis of a Stereochemically Defined 1,2-Diazetine-N,N'-Dioxide and a Study of Its Thermal Decomposition” Breton, G. W.; Oliver, L. H.; Nickerson, J. E. Journal of Organic Chemistry 2007, 72, 1412-1416.
“Thermal Decomposition of a Series of 1,2–Diazetines” Breton, G. W.; Shugart, J. H. Journal of Organic Chemistry 2003, 68, 8643-8649.
“Are 1,2-Dihydrodiazetes Aromatic? An Experimental and Computational Investigation” Breton, G. W.; Martin, K. L. Journal of Organic Chemistry 2002, 67, 6699–6704.
“Seed Chemistry of Sophora chrysophylla (Mamane) in Relation to Diet of Specialist Avain Seed Predator Loxioides bailleui (Palila) in Hawaii” Banko, P. C.; Cipollini, M. K.; Breton, G. W.; Pauk, E.; Wink M.; Izhaki, I. Journal of Chemical Ecology 2002, 28, 1393–1410.
“Synthesis of 1,2-Diazetines via a Diels-Alder Cycloaddition Approach” Breton, G. W.; Shugart, J. H.; Hughey, C. A.; Perala, S. M.; Hicks, A. D. Organic Letters 2001, 3, 3185–3187.
“Use of Cyclic Allylic Bromides in the Zinc-Mediated Aqueous Barbier-Grignard Reaction” Breton, G. W.; Shugart, J. H.; Hughey, C. A.; Conrad, B. P.; Perala, S. M. Molecules 2001, 6, 655-662.
“Further Studies of the Thermal and Photochemical Diels-Alder Reactions of N–Methyl–1,2,4–triazoline-3,5–dione (MeTAD) with Naphthalene and Some Substituted Naphthalenes” Breton, G. W.; Newton, K. A. Journal of Organic Chemistry 2000, 65, 2863–2869.
“Surface–Mediated Reactions. 8. Oxidation of Sulfides and Sulfoxides with tert-Butyl Hydroperoxide and OXONE” Kropp, P. J.; Breton, G. W.; Fields, J. D.; Tung, J. C.; Loomis, B. R. Journal of the American Chemical Society 2000, 122, 4280–4285.
“Acetylation of Unsymmetrical Diols in the Presence of Al2O3” Breton, G. W.; Kurtz, M. J.; Kurtz, S. L. Tetrahedron Letters 1997, 38, 3825–3828.
“Selective Monoacetylation of Unsymmetrical Diols using SiO2 Supported Sodium Hydrogen Sulfate” Breton, G. W. Journal of Organic Chemistry 1997, 62, 8952–8954.
“Surface–Mediated Reactions. 5. Oxidation of Sulfides, Sulfoxides, and Alkenes with tert–Butyl Hydroperoxide” Breton, G. W.; Fields, J. D.; Kropp, P. J. Tetrahedron Letters 1995, 36, 3825.
“Surface–Mediated Reactions. 6. Effects of Silica Gel and Alumina on Acid–Catalyzed Reactions” Kropp, P. J.; Breton, G. W.; Craig, S. L.; Crawford, S. D.; Durland, W. F.; Jones, III, J. E.; Raleigh, J. S. Journal of Organic Chemistry 1995, 60, 4146.
“Surface–Mediated Reactions. 3. Hydrohalogenation of Alkenes” Kropp, P. J.; Daus, K. A.; Tubergen, M. W.; Kepler, K. D.; Wilson, V. P.; Craig, S. L.; Baillargeon, M. M.; Breton, G. W. J. Journal of the American Chemical Chemistry, 115, 3071.
Scholarly Educational Articles
“Introduction of a Computational Chemistry Course-Based Undergraduate Research Experience (CURE) into an Advanced Organic Chemistry Lab: An Investigation of Propellane Formation" Alexander, P. J.; Button-Jennings, D.; Evans, C. N.; Hemstreet, M. B.; Henager, M. E.; Jacob, S.; Jolly, C. S.; Lantzman, M. R.; Saputo, A.; Stager, N. R.; Whitman, E. L.; Young, B. J.; Breton, G. W. World Journal of Chemical Education, 2021, 9, 88-93.
“The Synthesis of Isoamyl Acetate (Banana Oil) via an SN2 Reaction” Breton, G. W.
Chemical Educator, 2011, 16, 6-8.
“Electrophilic Aromatic Chlorination: Synthesis of the Fungicide Chloroneb” Breton, G. W. Chemical Educator, 2011, 16, 89-90.
“Free Radical Bromination of 2-Methylbutane and Analysis by 1H NMR Spectroscopy” Breton, G. W. Chem. Educator 2005, 10, 298-299.
“Multi-Week Synthesis of a Sunscreen Agent for the Organic Chemistry Laboratory” Breton, G. W.; Belk, M. K. Chem. Educator 2004, 9, 27-29.
"A Heated Cuvette Holder for Fiber-Optic Ultraviolet-Visible Spectrophotometers" Breton, G. W.; Kinzer, D.; Shugart, J. H. Chem. Educator 2003, 8, 199-200.
“Using Writing to Enhance the Undergraduate Research Experience” Bressette, A. R.; Breton, G. W. J. Chem. Ed. 2001, 78, 1626–1627.
“Student–Determined Values for the Calculation of Chemical Shifts of Methylene Protons in Different Chemical Environments” Breton, G. W. J. Chem. Ed. 2000, 77, 81–83.
“An Inexpensive Commercially Available Analog-to-Digital Converter” Breton, G. W. J. Chem. Ed. 2000, 77, 262.
“Investigating a Reaction of N–Methyltriazolinedione” Breton, G. W. The Chemical Educator 1999, 4, No. 4.
“A Grignard–Like Organic Reaction in Water” Breton, G. W.; Hughey, C. A. J. Chem. Ed. 1998, 75, 85–86.
“Photodimerization of Anthracene. A [4p+4p] Photochemical Cycloadddition” Breton, G. W.; Vang, X. J. Chem. Ed. 1998, 75, 81–82.
“Generation and Observation of Cyclopentadienyl Anion” Breton, G. W. The Chemical Educator 1997, 2, No. 6.
“The Wittig Reaction: Generation, Observation and Reactivity of a Phosphorous Ylide Intermediate. An Experiment for the Advanced Organic Chemistry Laboratory Course” Breton, G. W. J. Chem. Ed. 1997, 74, 114–115.
~Breton Publications~
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