J. Hodge Markgraf
1930 - 2007

Ebenezer Fitch Professor of Chemistry, Emeritus

Education

• Williams College, A.B., 1952
• Yale University, M.S., 1954
• Yale University, Ph.D., 1957
• University of Munich, postdoctorate, 1956-1957

Contact Information

• Office/Lab: 329 BSC
• Telephone: (413) 597-2204
• E-mail: j.hodge.markgraf@williams.edu

Courses Taught

• 251: Organic Chemistry: Intermediate Level
• 344: Physical Organic Chemistry
• 346: Heterocyclic Chemistry

Summer 2006 Research Students

• Ryan Gerrity '07
• Noah Lindquist '08

Research Interests

Carbazole Alkaloids

A novel and concise route to a family of carbazole alkaloids has been developed. Current studies are directed toward optimizing the processes.

 

 

Benzocanthinone Alkaloids

We have developed a new route to benzocanthinone (1), a pharmacologically-active alkaloid derived from plants. This methodology is currently being applied to the syntheis of analogs of 1.

 

 

Selected Publications

• Schofield, M. H.; Sorel, M.-A.; Manalansan, R. J.; Richardson, D. P.; Markgraf, J. H.  Substituent Effects on 15N and 13C NMR Chemical Shifts of 3-Phenylisoxazoles: a Theoretical and Spectroscopic Study. Magn. Reson. Chem. 2006, 44, 851-855.
• Markgraf, J. H.; Dowst, A. A.; Hensley, L. A.; Jakobsche, C. E.; Kaltner, C. J.; Webb, P. J.; Zimmerman, P. W.  A Versatile Route to Isomeric Benzocanthinones. Tetrahedron 2005, 61, 9102-9110.
• Crawley, M. L.; Hein, K. J.; Markgraf, J. H. Efficient Synthesis of 4,4-Dimethyl-1,9,10(1H)-anthracenetrione. J. Chem. Res. (S) 2003, 470-471.
• Truran, G. A.; Aiken, K. S.; Fleming, T. R.; Webb, P. J.; Markgraf, J. H. Solid Phase Organic Synthesis and Combinatorial Chemistry: A Laboratory Preparation of Oligopeptides. J. Chem. Educ. 2002, 79, 85-86.
• Markgraf, J. H.; Sangani, P. K.; Manalansan, R. J.; Snyder, S. A.; Thummel, R. P. Strained Heterocyclic Systems. Part 21. The Menschutkin Reaction. J. Chem. Res. (S) 2000, 561-563.
• Snyder, S. A.; Vosburg, D. A.; Jarvis, M. G.; Markgraf, J. H. Intramolecular Hetero Diels-Alder Routes to Carboline Alkaloids. Tetrahedron 2000, 56, 5329-5335.
• Markgraf, J. H.; Stickney, C. A. A New Synthesis of N-Phenyl Lactams. J. Heterocycl. Chem. 2000, 37, 109-110.
• Markgraf, J. H.; Choi, B. Y. Oxidation of Benzyl Ethers via Phase Transfer Catalysis. Synth. Commun. 1999, 29, 2405-2411.
• Markgraf, J. H.; Dubow, J. S.; Charland, J. A.; Sohn, E. H. Kinetic Isotope Effects in the Chromium (VI) Oxidation of Bicyclic Alcohols. J. Chem. Res. (S) 1999, 146-147.
• Markgraf, J. H.; Choi, B. Y. Oxidation of Benzyl Ethers via Phase Transfer Catalysis. Synth. Commun. 1999, 29, 2405-2411.
• Markgraf, J. H. Infrared Carbonyl Frequencies of Heterocyclic Lactones. Heterocycles 1998, 47, 559-624.
• Markgraf, J. H.; Snyder, S. A.; Vosburg, D. A. A Concise Route to Isocanthin-6-one. Tetrahedron Lett. 1998, 39, 1111-1112.
• Markgraf, J. H.; Choi, B. Y. An Aldehyde Derivative. J. Chem. Educ. 1998, 75, 222-223.
• Markgraf, J. H.; Chang, R.; Cort, J. R.; Durant, J. L., Jr.; Finkelstein, M.; Gross, A. W.; Lavyne, M. H.; Moore, W. M.; Petersen, R. C.; Ross, S. D. Protodediazoniation of Aryldiazonium Fluoroborates by Dimethylformamide, Tetrahedron 1997, 53, 10009-10018.
• Markgraf, J. H.; Sangani, P. K.; Finkelstein, M. Oxidation of Benzylamines to Amides. Synth. Commun. 1997, 27, 1285-1290.
• Markgraf, J. H.; Patterson, D. E. A Convenient Route to Heteronaphthacenes. J. Heterocycl. Chem. 1996, 33, 109-111
• Markgraf, J. H., Finkelstein, M.; Cort, J. R. Canthine Analogs via Intramolecular Diels-Alder Reactions. Tetrahedron 1996, 52, 461-470.