Wayne F. K. Schnatter  Associate Professor  Synthetic Organic Chemistry

Telephone
(718) 488-1453

E-mail
Wayne.Schnatter@liu.edu

EDUCATION

Postdoctoral Research Associate: University of California, Santa Barbara,
with Thomas C. Bruice

Postdoctoral Research Associate: University of Montreal, Montreal, Quebec, Canada,
with Stephen Hanessian

Ph.D., Chemistry: Princeton University
with Martin F. Semmelhack

M.A., Chemistry: Princeton University

B.S., Biology and Chemistry: Rensselaer Polytechnic Institute

I am interested in developing new transition metal based reactions for the synthesis of organic compounds. My research has focused on the development of stoichiometric reagents that are used in cyclization or cycloaddition reactions. Some sample reactions are provided below.

Cycloaddition reactions of 2-ethoxyvinylketene complexes with alkynes provide catechol ether derivatives. I am studying the substituent effects on the reaction as well as the range of alkynes that can undergo the reaction with some facility.

Furan ring formation has emerged as the dominant reaction of many iron(0) carbene complexes with alkynes of a wide variety of structural variation. I am in the process of establishing the range of alkynes for which this is true. Emphasis will be placed on varying the nature of the alkyne.

I am also interested in expanding our initial studies of the coupling reaction of geminal dihalides with Collman's Reagent. The nature of the intermediates may allow for the development of a general coupling reaction with dihalides or other derivatives.

Although much of the chemistry involves the use of iron complexes, I am aggressively seeking alternative systems to diversify my approach. Recent studies have been carried out with titanium, zirconium, chromium, and cobalt. I am especially interested in developing new catalytic systems for employment in total syntheses.

In addition to the methodology development, I am also interested in the use of molecules with rigid structures for use as scaffolds for nanostructure assembly. A series of cycloadditions will be used in this work.

Schnatter, W.F.K.; Rogers, D. W.; Zavitsas, A. A. "Electrophilic Aromatic Substitution: Enthalpies of Hydrogenation of the Ring Determine Reactivities of C₆H₅X. The Direction of the C₆H₅—X Bond Dipole Determines Orientation of the Substitution" J. Phys. Chem. A 2013, 117, 13079-13088.

Truong, J.; Caze, V.; Akhani, R. A.; Joshi, G. K.; Kakalis, L.; Matsunaga, N.; Schnatter, W.F.K. "Halogenated Catechols from Cycloaddition Reactions of η⁴-(2-ethoxyvinylketene)iron(0) Complexes with 1-Haloalkynes" Tetrahedron Lett. 2010, 51, 921.

Akhani, R. A.; Rehman, A.; "Incorporation of Hexafluorobutyne into Furans or Phenols via Reaction with Iron(0) Carbene or Vinylketene Complexes" Tetrahedron Lett. 2009, 50, 930.

Zhang, J.; Zhang, Y.; Schnatter, W.F.K.; Herndon, J. W. "Coupling of N-Heterocycle-Fused Enyne Aldehydes with γ,δ-Unsaturated Fischer Carbene Compl" Organometallics 2006, 25, 1279.

Darbasie, N.D.; Schnatter, W.F.K.; Warner, K. F.; Manolache, N. "The Cycloaddition Reactions of 2-Ethoxy-3-phenylvinylketene iron(0) with Alkynes to Yield Catechol Derivatives" Tetrahedron Lett. 2006, 47, 963.

Warner, K. F.; Rehman, A.; Jha, S.; Schnatter, W. F. K. "Coupling of Geminal Dihalides with Disodium Tetracarbonylferrate: A Novel Reactivity Pattern for Collman's Reagent" J. Chem. Res. (S) 1999, 514.

Warner, K. F.; Bachrach, A.; Rehman, A.; Schnatter, W. F. K.; Mitra, A.; Shimanskas, C. "A Practical Synthesis of 2,6-Dicarboxyfluorenone" J. Chem. Res. (S) 1998, 814.

Habib, M. S.; Speaker, M. G.; Schnatter, W. F. "Mass Spectrometric Analysis of the By-products of Intrastromal Photorefractive Keratectomy" Opthalm. Surgery and Lasers, 1995, 26, 481.

Herndon, J. W.; Tumer, S. U.; McMullen, L. A.; Matasi, J. J.; Schnatter, W. F. K. "Cyclopropylcarbene-chromium Complexes: Versatile Reagents for the Synthesis of Five-Membered Rings" Advances in Metal-Organic Chemistry 1994, 3, 51.

Rehman, A.; Schnatter, W. F. K.; Manolache, N. "Substrate Dependence of Benzene vs. Furan Ring Formation in the Reaction of Iron(0) Carbene Complexes" J. Am. Chem. Soc. 1993, 115, 9848.

Schnatter, W. F. K.; Almarsson, O.; Bruice, T. C. "The Synthesis of a Porphyrin with a Hydrocarbon Encapsulated Face" Tetrahedron, 1991, 47, 8687.

Herndon, J. W.; Tumer, S. U.; McMullen, L. A.; Matasi, J. J.; Schnatter, W. F. K.; Daitch, C. E. "Reactions of Cyclopropylcarbene-chromium Complexes" Comments on Inorg. Chem. 1990, 10, 1.

Semmelhack, M. F.; Park, J.; Schnatter, W.; Tamura, R.; Steigerwald, M.; "Coupling Reactions of Fischer-type Carbene Complexes of Iron" Chemica Scripta, 1987, 27, 509.

Herndon, J. W.; Tumer, S. U.; Schnatter, W. F. K.; "Cyclopentenones From the Reaction of Alkynes with Cyclopropylcarbene Chromium Complexes" J. Am. Chem. Soc. 1988, 110, 3334.

Semmelhack, M. F.; Tamura, R.; Schnatter, W. F. K.; Park, J.; Steigerwald, M.; Ho, S. "Carbene-metal Complexes. New Processes and Applications in Organic Synthesis" Studies in Org. Chem. 1986, 25, 21.

Semmelhack, M. F.; Tamura, R.; Schnatter, W. F. K.; Springer, J. "The Reaction of Alkynes with (Ethoxyalkylidene)tetracarbonyliron(0) Complexes" J. Am. Chem. Soc. 1984, 106, 5363.