Jeff Byers Presentations

* Denotes Middlebury student co-author

"Mechanistic studies on the decarboxylation of pyrroleacetic acids" Byers, J. H.; Berliner, J. L.* Poster Presented at ACS National Meeting, Salt Lake City, UT, Poster ORGN 155, 3/22/09.

"Radical intermediates in and additions to ruthenium polyene complexes", Keenan, J. J.*; Byers, J. H. Poster Presented at ACS National Meeting, Salt Lake City, UT, Poster CHED 845, 3/23/09.

"Radical Additions to Styrene Transition Metal Complexes", Presented at 32nd Reaction Mechanisms Conference, Chapel Hill, NC, 6/28/08.

"Radical Additions to Styrene-Transition metal Complexes", Byers, J. H.; Janson, N. J.*; Griswold, M. K.*; O'Mara, D. M.* Poster Presented at ACS National Meeting,, Boston, MA, Poster ORGN 556, 8/21/07.

"Radical Chemistry or Arenechromium Tricarbonyl and Cyclobutadieneiron Tricarbonyl Complexes", Byers, J. H.; Sontum, S. F.; Dimitrova, T. S.*; Huque, S.*; Zegarelli, B. M.*; Zhang, Y.*; Janson, N. J.* Poster Presented at 2006 EUCHEM Radical Conference, Bergen, Norway, 7/10/2006.

"Radical Reactions mediated by Cyclobutadieneiron Tricarbonyl", Byers, J. H.; Zhang, Y.*; Zegarelli, B.M.*; Dimitrova, T.*; Huque, S.*; Sontum, S. F. Presented at 2005 Pacifichem meeting, Honolulu, HI, 12/17/05.

"Radical Reactions mediated by Cyclobutadieneiron Tricarbonyl", Byers, J. H.; Zhang, Y.*; Zegarelli, B.M.*; Dimitrova, T.*; Huque, S.*; Sontum, S. F. Presented at 2005 EPSCOR Annual Meeting, Burlington, VT, 8/15/05.

"Radical Reactions mediated by Cyclobutadieneiron Tricarbonyl", Byers, J. H.; Zhang, Y.*; Zegarelli, B.M.*; Dimitrova, T.*; Huque, S.*; Sontum, S. F. Presented at National Organic Symposium, Salt Lake City UT, 6/12/05. Abstract A38.

"Radical Reactions of Cyclobutadiene Iron Tricarbonyl" Zegarelli, B.*; Byers, J. H. Presented at Pfizer Summer Research Fellow poster session, Groton, CT, 9/04.

"Radical Aromatic Substitution on Nitrogen Heterocycles" Byers, J. H.; Woo, G. W.*; Dewitt, A. J.*; Duff, M. P.*; Nasveschuk, C. G.* Presented at 19th International Congress of Heterocyclic Chemistry, Ft. Collins, CO Abstract 11-PO-27, 8/11/03.
"Advances in Radical Aromatic Substitution" Gordon Research Conference on Physical Organic Chemistry, Plymouth, NH, 7/3/03 (invited speaker).

"Activation of Benzene for Radical Addition in Organic Synthesis" Alexander, J. B.*; Byers, J. H. Presented at Posters on the Hill, Sponsored by the Council on Undergraduate Research, Washington, D. C., 4/1/03.

"Radical Reactions of Cyclobutadieneiron Tricarbonyl" Zhang, Y.*; Byers, J. H. Presented at Pfizer Summer Research Fellow poster session, Groton, CT, 10/4/02.

"Radical Additions to Nitrogen Heterocycles" Byers, J. H. Presented at Gordon Conference on Organic Reactions and Processes, Bristol, RI, 7/02.

"Syntheses of 3-Acylindoles via the Alkylation of the Dianion of 3-Acetylindole"; Zhang, Y.*; Byers, J. H. Presented at National Meeting of the American Chemical Society, Orlando FL, 4/02.

"Tandem Radical Additions to Indole and Pyrrole" Byers, J. H.; Kosterlitz, J. A.*; Nasveschuk, C. G.*; Steinberg, P. A.*, Northrop, B. H.* Presented at 37th National Organic Symposium, Bozeman, MT, 6/10/01, Paper No. 56.

"Tandem Radical Additions to Nitrogen Heterocycles" Byers, J. H.; Kosterlitz, J. A.*; Nasveschuk, C. G.*; Steinberg, P. A.* Presented at Pacifichem Meeting, Honolulu, HI 12/00.

"Attempted Radical Aromatic Substitution to Benzenoid Aromatics" DeWitt, A. J.*; Byers, J. H. Presented at Pfizer Summer Research Fellow poster session, Groton, CT, 9/00.

"Tandem Radical Additions to Nitrogen Heterocycles" Byers, J. H.; Kosterlitz, J. A.*; Nasveschuk, C. G.*; Steinberg, P. A.* Presented at Esther Humphrey Symposium, University of Vermont, Burlington, VT 9/30/00.

"Tandem Radical Additions to Nitrogen Heterocycles" Byers, J. H.; Kosterlitz, J. A.*; Nasveschuk, C. G.*; Steinberg, P. A.* Presented at Gomberg 2000 Symposium, University of Michigan, Ann Arbor, MI 6/29/00.

"Radical Aromatic Substitution via Atom-Transfer Addition" Byers, J. H.; Campbell, J. E.*; Knapp, F. H.*; Kosterlitz, J. A.*; Steinberg, P. L.*; Thissell, J. P.* Presented at Gordon Conference on Free Radical Reactions, Holderness, NH, 7/12/99.

"Control of Stereochemistry in Radical Aromatic Substitution via Atom-Transfer Addition" Wolkowski, J. P.*; Byers, J. H., Presented at 217th ACS National Meeting, Anaheim, CA, 3/22/99. Paper no. CHED-288.

"Radical Aromatic Substitution At Arene Chromium Tricarbonyl Complexes" Steinberg, P. L.*; Byers, J. H.; Neale, N. R.*, Presented at Pfizer Summer Research Fellow poster session, Groton, CT, 9/25/98.

"Radical Aromatic Substitution Via Atom-Transfer Addition" Byers, J. H.; Campbell, J. E.*; Knapp, F. H.*, Presented at 216th ACS National Meeting, Boston, MA, 8/24/98, Paper no. ORGN-594.

"Radical Aromatic Substitution At Arene Chromium Tricarbonyl Complexes" Steinberg, P. L.*; Byers, J. H.; Neale, N. R.*, Presented at 216th ACS National Meeting, Boston, MA, 8/24/98, Paper no. CHED-274.

"Control Of Stereochemistry In Radical Aromatic Substitution Via Atom-Transfer Addition" Wolkowski, J. P.*; Byers, J. H.; Burkett, G.C.*, Presented at 216th ACS National Meeting, Boston, MA, 8/24/98, Paper no. CHED-273.

"Intramolecular Reactions Involving Radical Aromatic Substitution Via Atom Transfer" Breen, C. A.*; Byers, J. H.; Kosterlitz, J. A.*, Presented at 216th ACS National Meeting, Boston, MA, 8/24/98, Paper no. CHED-272.

"Addition of Iodoesters to Aromatic Heterocycles" Knapp, F. H.*; Byers, J. H.; Thissell, J. G.* Presented at Pfizer Summer Research Fellow poster session, Groton, CT, 9/27/96.

"Radical Lactonizations at High Concentration"; Byers, J. H.; Shaughnessy, E. I.*; Mackie, T. N.*, Presented at CU Roche-Syntex Symposium, Boulder, CO, 5/22/96.

"Addition of Nucleophilic Radicals via Atom Transfer"; Whitehead, C. C.*; Byers, J. H.; Duff, M. E.*, Presented at 211th ACS National Meeting, New Orleans, LA, 3/26/96, Paper no. CHED-502.

"Addition of Phenylselenomalonates to Indole": Byers, J. H.; Thissell, J. G.*; Knapp, F. H.*, Presented at 211th ACS National Meeting, New Orleans, LA, 3/25/96, Paper no. ORGN-94.

"Intermolcular Radical Reactions Involving Phenyl Selenide Transfer" Byers, J. H., Presented at Esther Humphrey Symposium, Burlington, VT, 10/94.

"Addition of Nucleophilic Radicals via Atom Transfer"; Whitehead, C. C.*; Byers, J. H. Presented at Pfizer Summer Research Fellow poster session, Groton, CT, 9/94.

"A Novel Lactonization Procedure Involving Phenyl Selenide Transfer": Byers, J. H.; O'Leary, B. M.; Zraly, M. A., Presented at 24th Northeast Regional Meeting of the ACS, Burlington, VT, 6/22/94, Abstract no. 137.

"Carbon-Carbon Bond Formation in the Radical Addition Reactions of Phenyl Selenides to Alkenes and Alkynes": Byers, J. H.; Harper, B. C.; Lane, G. C.*; Schuman, D. S.*; Zraly, M. A.*, Poster presented at 23rd National Organic Symposium, Bozeman, MT, 6/93.

"Carbon-Carbon Bond Formation in the Radical Addition Reactions of Phenyl Selenides to Alkenes and Alkynes": Byers, J. H.; Harper, B. C.; Lane, G. C.*; Schuman, D. S.*; Zraly, M. A.*, Poster presented at 205th ACS National Meeting, Denver, CO, 3/31/93, Paper no. ORGN-197.

"Carbon-Carbon Bond Formation via Phenyl Selenenyl Transfer Radical Reactions"; Byers, J. H.; Lane, G.C.*; Gleason, T. G.*; Knight, K. S.*, Poster presented at 22nd National Organic Symposium, Minneapolis, MN, 6/16/91, Abstract no. A-29.

"Carbon to Carbon Bond Formation with Phenylselenide Transfer"; Lane, G. C.*; Byers, J. H. Presented at the Undergraduate Research Symposium, Rensselaer Polytechnic Institute, Troy, NY 4/20/91.

"Novel Synthesis of Carbon to Carbon Bonds via Phenylselenide Transfer"; Lane, G. C.*; Byers, J. H. Poster Presented at Fourth National Conference on Undergraduate Research, Schenectady, NY 4/20/90, Abstract no. CHM105.

"Free Radical Cyclization Reactions Using Boron Amine Initiators"; Ashfaq, A.*; Byers, J. H. Poster presented at Fourth National Conference on Undergraduate Research, Schenectady, NY, 4/20/90, Abstract no. CHM104.

"Synthesis and Pd(II) Catalyzed Reactions of Acylstannanes"; Pringle, W. C.*; Byers, J. H. Poster presented at Fourth National Conference on Undergraduate Research, Schenectady, NY, 4/20/90, Abstract no. CHM068.

"Intra- and Intermolecular Reactions Involving Phenyl Selenide Transfer"; Byers, J. H.; Gleason, T. G.*; Underwood, G. S.*; Lane, G. C.*, Poster presented at 8th Annual Esther Humphrey Symposium, Burlington, VT, 10/7/89.

"Radical Reactions Involving Phenyl Selenide Transfer"; Byers, J. H.; Gleason, T.*; Knight, K.*, Presented at 22nd Great Lakes Regional Meeting of the ACS, Duluth MN, 6/1/89, Abstract no. 92.

MiddTags:

Jeff Byers Publications

* Denotes Middlebury College undergraduate co-authors

"Radical Aromatic Substitution with Benzene Chromiumtricarbonyl" Byers, J. H.*; Neale, N. R.*; Alexander, J. B.* Gangemi, S. P.* Tetrahedron Lett. 2007, 48, 7903-7905.

"The Radical Addition of Dimethyl 2-Ethynylcyclopropane-1,1-dicarboxylate to Electron-Rich Olefins" Byers, J. H.; Goff, P. H.*; Janson, N. J.*; Mazzotta, M. G.*; Swigor, J. E. Synthetic Commun. 2007, 37, 1865-1871.

"Radical Additions to (n6-Styrene) Chromium Tricarbonyl" Byers, J. H.; Janson, N. J.* Organic Lett. 2006, 8, 3453.

"Thiocarbonyldiimidazole" Byers, J.H. Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed. Wiley, 2006.

"Radical Reactions Mediated by Cyclobutadieneiron Tricarbonyl" Byers, J. H.; Sontum, S. F.; Dimitrova, T. S.*; Huque, S.*; Zhang, Y.*; Zegarelli, B. M.*; Jasinski, J. P; Butcher, R. P. Organometallics 2006, 25, 3787.

"Tandem Radical-Electrophilic Annulations to Pyrrole" Byers, J. H.; DeWitt, A.*; Nasveschuk, C. G.*; Swigor, J. E. Tetrahedron Lett., 2004, 45, 6587-6590.

"A One-step Radical Synthesis of Pyrrol-2-Acetic Acids" Byers, J. H.; Duff, M. P.*; Woo, G. W.*, Tetrahedron Lett., 2003, 44, 6853-6855 .

"Syntheses of 3-Acylindoles via the Alkylation of the Dianion of 3-Acetylindole" Byers, J. H.; Zhang, Y.* Heterocycles, 2002, 57, 1293-1297.

"Tandem Radical Addition Reactions to Substituted indoles Under Atom-Transfer and Oxidative Conditions" Byers, J. H.; Kosterlitz, J. A.*; Steinberg, P. A.* Comptes Rendus de L'Academie Des Sciences - Serie II c - Chimie, 2001, 4, 471.

"Atom Transfer Reactions" Byers, J. H. in Radicals in Organic Synthesis, M. P. Sibi and P. Renaud, eds. Wiley-VCH, 2001.

Book Review by Byers, J. H.: "General Aspects of Free Radical Chemistry", Z. B. Alfassi, ed. in J. Chem. Ed., 2000, 77, 565.

"Radical Aromatic Substitution via Atom-Transfer Addition"; Byers, J. H.; Campbell, J. E.*; Knapp, F. H.*; Thissell, J. G.* Tetrahedron Lett., 1999, 40, 2677.

"Radical Lactonizations at Anomalously High Concentrations"; Byers, J. H.; Shaughnessy, E. I.*; Mackie, T. N.* Heterocycles, 1998, 48, 2071.

"A Novel Radical-Based Synthesis of Valerolactones"; Byers, J. H.; O'Leary, B. M.*; Zraly, M. A.* Synthetic Commun., 1996, 26, 4039.

"Addition of a Sulfur-Stabilized Radical to Electron-Deficient Alkenes via Phenyl Selenide Transfer"; Byers, J. H.; Whitehead, C.C.*; Duff, M. E.* Tetrahedron Lett. 1996, 37, 2743.

"The Synthesis of Geminal Diphosphonates via Phenyl Selenide Transfer"; Byers, J. H.; Thissell, J. G.*; Thomas, M. A.* Tetrahedron Lett. 1995, 36, 6403-6406.

"The Photochemical Disproportionation of Dialkyl 2,2-Di(phenylseleno) Malonate"; Byers, J. H.; Thissell, J. S.* Synthetic Commun. 1995, 25, 21-26.

"Diphenyl Diselenide" Byers, J. H. Encyclopedia of Reagents for Organic Synthesis. Paquette, L., Ed.

"Diphenyl Disulfide" Byers, J. H. Encyclopedia of Reagents for Organic Synthesis. Paquette, L., Ed.

"Radical Addition Reactions of 2-Phenylselenopropanedioates to Alkenes and Alkynes"; Byers, J. H.; Lane, G. C.* J. Org. Chem. 1993, 58, 3355-3360.

"Radical Addition of Varied Functionality via Phenylselenenyl Transfer"; Byers, J. H.; Harper, B. C.* Tetrahedron Lett. 1992, 6953-6954.

"Hexenyl Radical Cyclization via Phenyl Selenide Transfer"; Byers, J. H.; Gleason, T. G.*; Knight, K. S.* Chem. Commun. 1991, 355-357.

"A Convenient Preparation of O-Acyl Formaldehyde Cyanohydrins"; Byers, J. H.; Baran, R. C.*; Craig, M. E*; Jackman, J. T.* Org. Prep. and Proc., Int. 1991, 373.

"The Palladium-Catalyzed Oxidation of 2-Vinylnaphthalene: A Microscale Organic Experiment"; Byers, J. H.; Ashfaq, A. A.*; Morse, W.* J. Chem. Ed. 1990, 67, 341-342.

"Radical Addition of Diethyl (2-Phenylseleno)propanedioate to Olefins"; Byers, J. H.; Lane, G. C.* Tetrahedron Lett. 1990, 5697-5701.

"An Improved Preparation of Gamma-Keto Cyclobutanones"; Kaydos, J.; Byers, J. H.; Spencer, T. A. J. Org. Chem. 1989, 54, 4698-4700.

"A Free-Radical Addition-Fragmentation Reaction for the preparation of Vinyl Sulfones and Phosphine Oxides"; Keck, G. E.; Byers, J. H.; Tafesh, A. M. J. Org. Chem. 1988, 53, 1127-1128.

"A New One Electron Carbon-Carbon Bond Forming Reaction: Separation of the Chain Propagation Steps in Free-Radical Allylation"; Keck, G. E.; Byers, J. H. J. Org. Chem. 1985, 50, 5442.

"A Novel 1,4 Cyclohexanone Annulation." Byers, J. H.; Spencer, T. A. Tetrahedron Lett. 1985, 713-716.

"Improved Preparation and New Reactions of ß(1-Phenylthio)cyclopropyl Enones." Byers, J. H.; Spencer, T. A. Tetrahedron Lett. 1985, 717-720.

 

MiddTags:

Jeff Byers' Research

My research program at Middlebury is carried out entirely with the assistance of undergraduate students.  Through a variety of other internal and external funding sources, I typically have 3-4 students working side-by-side with me each summer, with a comparable number during the academic year.  Since beginning my career at Middlebury in 1986, I have been awarded one grant from The Research Corporation, two ACS/PRF grants, four NSF-RUI grants, and served as PI or co-PI on NSF instrumentation grants leading to the acquisition of an NMR, GC/MS, polarimeter, and LC/MS for use in research and course based-activities.  With these grants, I have been able to involve over 80 undergraduate students in my research efforts.  Among these students, 24 went on to earn advanced degrees (mostly PhD's) in chemistry, biochemistry, or related fields, or are currently enrolled and progressing towards this degree.  A total of 27 of my former students have gone on to careers as physicians, with many of them gravitating towards research-based careers, and 4 have earned law degrees, and have established careers in patent law, putting the technical training which they received in the course of their research to use in a different venue.

The research which I and my students undertake is in the area of radical-based synthetic organic chemistry.  In the course of this research, we hope to discover new pathways by which organic molecules (consisting primarily, but not entirely, of Carbon and Hydrogen) can react. Much of this work has culminated in publications and presentations at scientific meetings with Middlebury students as coauthors.

During the last 30 years there has been a resurgence of interest in the development and use of radical reactions. Synthetic organic chemists have become aware of and interested in the potential power of radical reactions, which can often accomplish transformations which are impossible using classic ionic or pericyclic reactions.  Our long-term research goals center on the discovery of new radical reactions, and their application to carbon-carbon bond-forming processes of general value to synthetic organic chemists.  The use of transition-metal complexes to modify the reactivity of organic molecules, particularly polyenes, has been of great interest to organic chemists since the discovery of ferrocene over 50 years ago.  We have noted that there has been very little work at the interface of these two somewhat disparate fields.

Some of the larger questions we will be asking include:

  • Can these radicals even be generated?
  • Can ligand based, rather than metal based reactivity be ensured?
  • Will polyene complexation render radicals more or less reactivity?
  • How will complexation affect selectivity?
  • Can complexation be used to control stereoselectivity?

 

 

Jeff Byers

Philip Battell Stewart and Sarah Frances Cowles Stewart Professor of Chemistry

 
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 Spring 2015: Mon and Fri: 11:05AM - 12:00PM, Thurs 11:00-11:45AM, and by appointment
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