~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. https://doi.org/10.1002/047084289X.rh034 

“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. https://doi.org/10.1002/047084289X.rh035

“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. https://doi.org/10.1002/047084289X.rh039 

“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. https://doi.org/10.1002/047084289X.rh029.pub2 

~Scholarly Research Articles~ 

*undergraduate co-author

^internal collaborator

°external collaborator

"Improvement Upon a Largely Forgotten Method for the Synthesis of N-Alkyl Urazoles" Dean*, C. B., Jones*, A. B., Silvers*, O. N., Travis*, A. J., Zohbe*, B. L., Breton, G. B. Reactions 2026, 7, 27. https://doi.org/10.3390/reactions7020027

"What Causes Carbon-Centered Radicals to Pyramidalize? It Depends on the Type of Radical" Breton, G. W. Journal of Organic Chemistry 2026, 91, 904.  https://doi.org/10.1021/acs.joc.5c02141

"The Effects of Substituents on the Stabilities of Bridgehead Radicals" Breton, G.W.  Journal of Physical Organic Chemistry 2025, 38, e70036.  https://doi.org/10.1002/poc.70036

"Computational prediction of some properties of 3-substituted cyclooctynes and assessment of their synthetic accessibility via anionic vinyl bromide precursors" Bollwerk*, P., Hendrix*, T., Ivester*, P., Lynch*, S.N., Maddox*, G., McCloy*, C., Meeks*, R., Mintz*, B., Moore*, W.L., Reddersen*, H.M., Scholl*, C., Simpson*, A., Sylvie*, J.D., Teague*, V.N., Toole*, I.K., Wilkes*, N.L., Breton, G.W.​ PeerJ Organic Chemistry 2025, 7 e:14.  https://doi.org/10.7717/peerj-ochem.14

"The Importance of Strain on the Relative Energies of Bridgehead Radicals" Breton, G.W.  Journal of Physical Organic Chemistry 2025, 38, e70004.

https://doi.org/10.1002/poc.70004

"Paddlanes revisited: Which are the smallest possible?" Breton, G.W.  Journal of Physical Organic Chemistry 2024, 37, e4644. https://doi.org/10.1002/poc.4644 

"Frustrated Alternative Approaches Towards the Synthesis of a Thermally Stable 1,2-Diazacyclobutene" Breton, G.W.; Martin^, K.L. Molecules 2024, 29, 4068. https://doi.org/10.3390/molecules29174068.

“Spontaneous Formation of Strained Anti-Bredt Bridgehead Alkenes upon Computational Geometry Optimization of Bicyclic beta-Halo Carbanions” Breton, G.W., Ridlehoover*, J.V. Organics 2024, 5, 205-218.  https://doi.org/10.3390/org5030010 

"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 [publication resulting from a class project in Advanced Organic Chemistry course]

"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" and 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. https://doi.org/10.3390/M1578 [Invited manuscript for the special issue "Structure Determination" and selected to be highlighted 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. Chemistry: A European Journal 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. https://doi.org/10.1002/poc.3808

"DFT study of ortho, meta and para-pyridyl cations.  Pyridynium found?" Breton, G. W. Computational and Theoretical Chemistry 2018, 1173, 51-57. https://doi.org/10.1016/j.comptc.2018.04.013

"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.https://doi.org/10.1107/S2053229618005211 

"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. https://doi.org/10.1107/S2053229617010786 

“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. https://doi.org/10.1021/acs.jpca.6b03119 

“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. https://doi.org/10.1021/acs.joc.5b02520 

“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. https://doi.org/10.1021/acs.joc.5b00766 

“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.https://doi.org/10.1021/jo5014096

“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. https://doi.org/10.1016/j.tetlet.2014.06.091 

“Convenient Synthesis of Monobenzylated Hydrazides via Aqueous Zinc-Mediated Addition Reactions” Breton, G. W. Synthetic Communications 2014, 44, 1128-1136. https://doi.org/10.1080/00397911.2013.851245 

“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. https://doi.org/10.1021/jo4001417 

“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. https://10.5923/j.ajoc.20120206.02

“One-Pot Synthesis of Novel 2,3-Dihydro-1H-indazoles” Breton, G. W.; Lepore*, A. J. Molecules 2011, 16, 9553-9561. https://doi.org/10.3390/molecules16119553 

“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. https://doi.org/10.1016/j.tetlet.2010.12.024 

“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. https://doi.org/10.1021/ol0710414 

“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. https://doi.org/10.1021/jo062357c 

“Thermal Decomposition of a Series of 1,2–Diazetines” Breton, G. W.; Shugart*, J. H. Journal of Organic Chemistry 2003, 68, 8643-8649. https://doi.org/10.1021/jo0351926

“Are 1,2-Dihydrodiazetes Aromatic? An Experimental and Computational Investigation” Breton, G. W.; Martin^, K. L. Journal of Organic Chemistry 2002, 67, 6699–6704. https://doi.org/10.1021/jo026082m 

“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. https://doi.org/10.1023/A:1016248502927 

“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. https://doi.org/10.1021/ol0164942 

“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. https://doi.org/10.3390/60800655 

“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. https://doi.org/10.1021/jo9906429 

“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. https://doi.org/10.1021/ja9940569 

“Acetylation of Unsymmetrical Diols in the Presence of Al2O3” Breton, G. W.; Kurtz*, M. J.; Kurtz*, S. L. Tetrahedron Letters 1997, 38, 3825–3828. https://doi.org/10.1016/S0040-4039(97)00756-9 

“Selective Monoacetylation of Unsymmetrical Diols using SiO2 Supported Sodium Hydrogen Sulfate” Breton, G. W. Journal of Organic Chemistry 1997, 62, 8952–8954. https://doi.org/10.1021/jo971367y 

“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. https://doi.org/10.1016/0040-4039(95)00688-9 

“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. https://doi.org/10.1021/jo00118a035 

“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 1993, 115, 3071. https://doi.org/10.1021/ja00061a005 

~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. https://10.12691/wjce-9-3-4  [publication resulting from a class project in Advanced Organic Chemistry course]

“The Synthesis of Isoamyl Acetate (Banana Oil) via an SN2 Reaction”  Breton, G. W. Chemical Educator 2011, 16, 6-8. http://chemeducator.org/bibs/0016001/16110006.htm 

“Electrophilic Aromatic Chlorination:  Synthesis of the Fungicide Chloroneb”  Breton, G. W. Chemical Educator 2011, 16, 89-90. http://chemeducator.org/bibs/0016001/16110089.htm 

“Free Radical Bromination of 2-Methylbutane and Analysis by 1H NMR Spectroscopy” Breton, G. W. Chemical Educator 2005, 10, 298-299. http://chemeducator.org/bibs/0010004/1040298gb.htm 

“Multi-Week Synthesis of a Sunscreen Agent for the Organic Chemistry Laboratory” Breton, G. W.; Belk*, M. K. Chemical Educator 2004, 9, 27-29. http://chemeducator.org/bibs/0009001/910027gb.htm 

"A Heated Cuvette Holder for Fiber-Optic Ultraviolet-Visible Spectrophotometers" Breton, G. W.; Kinzer^, D.; Shugart*, J. H. Chemical Educator 2003, 8, 199-200. http://chemeducator.org/bibs/0008003/830199gb.htm

“Using Writing to Enhance the Undergraduate Research Experience”  Bressette^, A. R.; Breton, G. W. Journal of Chemical Education 2001, 78, 1626–1627. https://doi.org/10.1021/ed078p1626 

“Student–Determined Values for the Calculation of Chemical Shifts of Methylene Protons in Different Chemical Environments” Breton, G. W Journal of Chemical Education 2000, 77, 81–83.https://doi.org/10.1021/ed077p81 

“An Inexpensive Commercially Available Analog-to-Digital Converter”  Breton, G. W. Journal of Chemical Education 2000, 77, 262. https://doi.org/10.1021/ed077p262 

“Investigating a Reaction of N–Methyltriazolinedione” Breton, G. W. The Chemical Educator 1999, 4, No. 4. http://chemeducator.org/bibs/0004004/00040134.htm 

“A Grignard–Like Organic Reaction in Water” Breton, G. W.; Hughey*, C. A. Journal of Chemical Education 1998, 75, 85–86. https://doi.org/10.1021/ed075p85 

“Photodimerization of Anthracene.  A [4pi+4pi] Photochemical Cycloadddition” Breton, G. W.; Vang*, X. Journal of Chemical Education.  1998, 75, 81–82. https://doi.org/10.1021/ed075p81 

“Generation and Observation of Cyclopentadienyl Anion” Breton, G. W. The Chemical Educator 1997, 2, No. 6. https://doi.org/10.1007/s00897970152a 

“The Wittig Reaction:  Generation, Observation and Reactivity of a Phosphorous Ylide Intermediate.  An Experiment for the Advanced Organic Chemistry Laboratory Course” Breton, G. W. Journal of Chemical Education 1997, 74, 114–115. https://doi.org/10.1021/ed074p114