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John J. Eisch
- Distinguished Professor Emeritus, Organic (from 2013) Chemistry
CONTACT INFORMATION:

Department of Chemistry
State University of New York at Binghamton
Binghamton, NY 13902

e-mail : jjeisch@binghamton.edu
Phone : (607) 777 4261

PROFESSIONAL BACKGROUND


• B.S., summa cum laude, Marquette University, 1952
• Ph.D., Iowa State University, 1956, with Professor Henry Gilman
• Postdoctoral Fellow with Nobel Laureate Karl Ziegler, Max Planck Institut für Kohlenforschung (Mülheim), Germany 1956 -1957
• European Research Associates Fellow, Brussels, Belgium 1957, Union Carbide Corp.
• Research Fellow, Japan Society for the Promotion of Science, 1979, Kyoto University
• Distinguished Professor Chemistry, 1983
• Alexander von Humboldt Senior Scientist Research Award, Universität München, Germany 1993-1996
• First Henry Gilman Research Award, Iowa State University, 1995
• Doctor of Science, honoris causa, Marquette University, 2002
• Alexander von Humboldt Senior Scientist Continuing Research Award, Technische Universität, Germany 2005-2006
• Distinguished Professor of Chemistry Emeritus, 2013
RESEARCH INTERESTS
Our current research embraces a variety of studies on synthesis and reaction mechanism in organometallic and heterocyclic chemistry. Such interests in organometallic chemistry encompass the following aspects: 1) the stereoselective formation of carbon-carbon and carbon-hydrogen bonds by means of main-group or transition metal alkyls; 2) fundamental studies of Ziegler-Natta catalytic alkylations and oligomerizations, essential to industrial polymer and hydrocarbon technology; 3) the utility of subvalent organotransition-metal reagents in organic synthesis, especially in the homogenous desulfurization of sulfides and thiols (important for future chemical processes based on coal); 4) the generation of subvalent early transition metal reductants and their utility in organic synthesis and catalysis; and 5) unusual pericyclic or anionic rearrangments, such as those interconverting various transition metal, boron and aluminum compounds or the 1,n shifts observed in silicon and lithium compounds. Finally, this investigator has edited and composed Volumes 2, 3, and 4 of "Organometallic Syntheses," a treatment of research techniques and a compilation of reliable synthetic procedures for many organometallic compounds.

In heterocyclic studies we have been concerned with the synthesis and properties of unusual rings containing metals or nitrogen as ring constituents. Illustrative are five-membered (borole) and seven-membered (borepin) boron rings, which display antiaromatic and aromatic character, respectively. Furthermore, nitrogen heterocycles isoelectronic with azulenes have been found to display chromoisomerism (tautomeric equilibira between colorless and highly colored isomers), and the highly reactive, antiaromatic dibenzazapentalene and 1,2-diazacyclobutadiene systems have been synthesized for the first time. The results of such studies are expected to shed light on pi-electron interactions between carbon centers and various potential pi-bonding metals or nitrogen centers.

A most recent developing interest in our research has been a study of how amino acids, sugars and lipids were evolved on the prebiotic earth, thereby setting the stage for the chemical evolution of the RNA World and the emergence of Life. Particular attention has been given to the elaboration of sugar alcohols from the transition metal-catalyzed, photochemical redox reactions of formaldehyde.
SELECTED PUBLICATIONS (from 383 total)

  1. “Palladium-Catalyzed Carbon-Nitrogen and Carbon-Carbon Bond-Forming Reactions: Progress, Applications and Mechanistic Studies”, Brochure for the First Annual John Eisch Lectureship in Organic Synthesis, S.L. Buchwald, J.J. Eisch and E. Rozners, October 26, 2012.

  2. “6,12-Diphenyldibenzo[b,f]-[1,5]diazocine as an Electron-Capture Agent: Efficient Mechanistic Probe for SET Processes and Novel Reagent for the Oxidative Dimerization of Benzylic Organometallics”, J.J. Eisch, K. Yu and A.L. Rheingold, Eur. J. Org Chem., 3165-3171 (2012).

  3. “Distinguished colleagues, Chemistry Department honor Eisch and former students,” K. Ellis, with J.J. Eisch, Inside, November 8, 2011, 4 pp. A PDF of this presentation is available at the following link: http://www2.binghamton.edu/chemistry/news/eisch-symposium.html

  4. “Rearrangements of Imine Radical-Anions in the [1,4]-and [1,5]-Diazocine Systems”, K. Yu, W. Liu, J.J. Eisch and A.L. Rheingold, John Eisch Organometallic Symposium, poster available as a manuscript, 9 pp.

  5. “Retrospect, Prospect and Gratitude”: Valedictory, J.J. Eisch, Proceedings of the John Eisch Organometallic Symposium, SUNY-Binghamton, October 29, 2011, 8 pp. A PDF of this presentation is available at the following link: http://www2.binghamton.edu/chemistry/news/eisch-symposium/eisch.pdf

  6. “The Pleasure of Finding Things Out”: Laudatio in honor of Professor John Eisch and his former research students, U.H. Brinker, with J.J. Eisch, Proceedings of the John Eisch Organometallic Symposium, SUNY-Binghamton, October 28, 2011, 27 pp. A PDF of this presentation is available at the following link: http://www2.binghamton.edu/chemistry/news/eisch-symposium/brinker.pdf

  7. Publisher Correction to “Fifty Years of Ziegler-Natta Polymerization: From Serendipity to Science. A Personal Account”, J.J. Eisch, Organometallics, 31, 6504 (2012).

  8. “Fifty Years of Ziegler-Natta Polymerization: From Serendipity to Science. A Personal Account.”, J.J. Eisch, Organometallics, 31, 4917-4932, (2012).

  9. “Nobel Prize in Chemistry 1963: Karl Ziegler and Guilio Natta”, J.J. Eisch with J.E. LaBonté, Cover Graphic Art, Issue 14, Organometallics, July 23, 2012.

  10. “Versatile Zirconium Reductants and Carbon-Carbon Coupling Agents Selectively Accessible From the 2:1 Molar Aggregate of n-Butyllithium and Zirconium(IV) Salts”, J.J. Eisch, J.N. Gitua and K. Yu, Eur.J. Org Chem., 3523-3530 (2011).

  11. “Dimerizing or Cyclizing C-C Bond Formation via C-H bond Activation by Prior Zirconation”, J.J. Eisch and S. Dutta, Organometallics, 23, 4181-4183 (2004). Correction: J.J. Eisch and K. Yu, Organometallics, DOI: 10:1021/om 200130w (2010).

  12. “Chemical Detection of Carbon-metal Bonds: From Distinct sigma-bonding of Main-Group Metals to Ambiguous pi-Bonding with Transition Metals, John J. Eisch, Inorg. Chim. Acta, 364, 3-9 (2010)

  13. “Novel Alkylidenating Agents of Iron(III) Derivatives via Base-Mediated α,μ-Dehydrohalogenation and Their Chemical Trapping by Cycloaddition”, J.J. Eisch, J.U. Sohn and E.J. Rabinowitz, Eur. J. Org. Chem., 2971-2977 (2010).

  14. “Festschrift in Honor of John M. Birmingham on his Eightieth Birthday: A Collection of Current Zirconocene Research Articles”, J.J. Eisch and E-i. Negishi, Editors, Dept. of Chemistry, SUNY-Binghamton, October 27, 2009, 250 pp.

  15. “Attempted Generation of the Potentially Aromatic 6,7-Diphenyldibenzo[e,g][1,4]-diazocine Dianion Leads with Profound Rearrangement to the Isomeric N-(2-Amino-1,2-Diphenylethenyl)carbazole Dianions”, J.J. Eisch, R.N. Manchanayakage and A.L. Rheingold, Org. Lett., Vol. 11, No. 18, 4060-4063 (2009).

  16. “Vanadium(I) Chloride and Lithium Vanadium(I) Dihydride as Selective Epimetallating Reagents for π- and σ-Bonded Organic Substrates”, J.J. Eisch and P.O. Fregene, Eur. J. Org. Chem., 4482-4492 (2008), Correction: J.J. Eisch and P.O. Fregene, Eur. J. Org. Chem., 1631 (2009).

  17. “Vanadium(I) Chloride and Lithium Vanadium(I) Dihydride as Selective Epimetallating Reagents for π- and σ-Bonded Organic Substrates”, J.J. Eisch and P.O. Fregene, Eur. J. Org. Chem., 4482-4492 (2008).

  18. “Vanadium(I) Chloride and Lithium Vanadium(I) Dihydride as Epimetallating Reagents for Unsaturated Organic Substrates: Constitution and Mode of Reaction”, J.J. Eisch, P.O. Fregene and D.C. Doetschman, Eur. J. Org. Chem., 2825-2835 (2008).

  19. “Purported Synthesis of 3,4,7,8-Tetraphenyl-1,2,5,6-Tetraazocine from Benzil and Hydrazine: Competing Cyclizations and Carbon-Carbon sigma-Bond Scissions”, J.J. Eisch, T.Y. Chan and J.N. Gitua, Eur. J. Org. Chem., 392-397 (2008).

  20. “End-Capped Polymers and Compositions Containing Such Compounds”, J.F. Kay and J.J. Eisch, U.S. Patent No. 7,241,813, July 10, 2007.

  21. “The Epimetallation and Carbonation of Carbonyl and Imino Derivatives: Epivanadation Route to 2-Amino and 2-Hydroxy Acids”, J.J. Eisch, P.O. Fregene and J.N. Gitua, J. Organomet. Chem., 692, 4647-4653 (2007).

  22. “End-Capped Polymers and Compositions Containing Such Compounds”, J.F. Kay and J.J. Eisch, U.S. Patent No. 7,205,337, April 17, 2007.

  23. “A Cautionary Tale on Reproducibility”, J.J. Eisch and B. Halford, Chem. & Eng. News, January 22, 2007, 85, 36 (2007).

  24. "Nickel(II)-Carbene Intermediates in Reactions of Geminal Dihaloalkanes with Nickel(0) Reagents and the Corresponding Carbene Capture as the Phosphonium Ylide", J.J. Eisch, Y. Qian and A.L. Rheingold, Eur. J. Inorg. Chem., 1576-1584 (2007).

  25. “The Transient Titanocene(II): Direct Synthesis from Solvated Titanium(II) Chloride and Cyclopentadienylsodium and Ensuing Interception with Diphenylacetylene as 1,1-Bis(cyclopentadienyl)-2,3,4,5-tetraphenyltitanacyclopentadiene", J.J. Eisch, A.A. Adeosun and J. M. Birmingham, Eur. J. Inorg. Chem., 39-43 (2007).

 
 
© Department of Chemistry, State University of New York at Binghamton, Binghamton, NY 13902-6000
updated, February 2013