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Joseph J. Tufariello

Professor Emeritus
Office: 678 Natural Sciences Complex
Phone: (716) 645-4253
E-mail: chejjt@buffalo.edu

Education:

B.S. Queens College (1957)
Ph.D., University of Wisconsin (1961)
Postdoctoral Fellow, Purdue University (1962)
NIH Postdoctoral Fellow, Cornell University (1963)

History and Overview of Interests:

Professor Tufariello retired in 2003. He retains an active interest in chemistry and, of course, the department. Professor Tufariello’s research focused on reactions of 1,3-dipolar compounds; synthesis of natural products; organometallic chemistry; synthesis and chemistry of strained or otherwise unique carbocyclic systems.

Professor Tufariello established an endowment in honor of his parents, The Joseph and Louise K. Tufariello Fund, used to present an award at graduation to the outstanding graduating senior as determined by a departmental committee named by the chairperson.

Specializations:

Reactions of 1,3-dipolar compounds; synthesis of natural products; organometallic chemistry; synthesis and chemistry of strained or otherwise unique carbocyclic systems.

Research Summary:

Our principal research interests focused in the area of organic synthesis. We explored the uses of 1,3-dipolar compounds as key intermediates in the synthesis of natural products. Our initial investigations centered on the use of nitrones in alkaloid synthesis.

More recently, we directed attention to the preparation of ß-lactams and to the synthesis of terpenoids and other nitrogen-free systems. Nitrone cycloadditions are cyclizations which result in the formation of carbon-carbon and carbon-oxygen bonds. These reactions incorporate considerable regioselectivity and stereoselectivity, and are especially suited to the synthesis of certain natural systems. The alkaloidal and terpenoid systems currently under investigation include several with profound and useful physiological activity.

Additionally, we have interests in the synthesis and reactivity of strained, or otherwise unique, carbocyclic compounds.

Finally, our research has included investigations of new synthetic methods, especially those involving the use of organometallics such as organoborane, organomercury, organolead, and organotitanium reagents.

Selected Publications:

  1. J. Tufariello, “Alkaloids from Nitrones,” Accounts of Chemical Research 12, 396 (1979).
  2. J. Tufariello and G. E. Lee, “Functionalized Nitrones. A Highly Stereospecific and Regioselective Synthesis of dl-Retronecine,” J. Am. Chem. Soc.102, 373 (1980).
  3. J. Tufariello, ” Nitrones in 1,3-Dipolar Cycloaddition Chemistry,” A. Padwa, Ed., Vol. 2, John Wiley and Sons 1984, p. 83-167.
  4. J. Tufariello, H. Meckler, and K. P. Senaratne, “The Use of Nitrones in the Synthesis of Anatoxin-a, Very Fast Death Factor,” in Tetrahedron, Symposium in Print 17, 3447 (1985).
  5. J. Tufariello and J. M. Puglis, “The a,a’-Dialkylation of Cyclic Amines. The Synthesis of Solenopsis Ant Venoms,” Tetrahedron Letters 1489 (1986).
  6. J. Tufariello and K. Winzenberg, “A Nitrone-Based Synthesis of the Pyrrolizidine Alkaloid Croalbinecine,” Tetrahedron Letters 1645 (1986).
  7. J. Tufariello, H. Meckler, and K. Winzenberg, “Synthesis of the Lolium Alkaloids,” J. Org. Chem. 51, 3557 (1986).
  8. J. Tufariello, A. S. Milowsky, M. Al-Nuri, and S. Goldstein, “The Synthesis and Cycloaddition Reactions of 3-Azabicyclo[3.1.0]hex-2-ene 3-oxide and 3-Azabicyclo[3.2.0]hept-2-ene 3-oxide. Highly Strained Nitrones,” Tetrahedron Letters 267 (1987).
  9. J. Tufariello, A. S. Milowsky, M. Al-Nuri, and S. Goldstein, “A Highly Selective Synthesis of (E,E)-1,5-Dienes,” Tetrahedron Letters 263 (1987).
  10. Ding and J. J. Tufariello, “A Facile Synthesis of Pyrrolines,” Synth. Commun. 20, 227 (1990).
  11. Ghosal, M. Samoc, P. Prasad, and J. J. Tufariello, “Study of Optical Nonlinearities of Organometallic Structures: Aryl and Vinyl Derivatives of Ferrocene,” J. Phys. Chem., 94, 2847-51 (1990).