Mark A. Forman, Ph.D.
Professor and Chair of Chemistry
Specialization: Organic Chemistry
Office: Science Center 403A
Phone: (610) 660-1781
Fax: (610) 660-1783
I graduated with a B.A. in Chemistry from Franklin and Marshall College (F&M) in 1986. While at F&M, I conducted undergraduate research on “The Thermal Rearrangement of endo-7-methyl-exo-7-vinylbicyclo[3.2.0]hept-2-ene,” under the direction of Dr. Phyllis Leber, Dr. E. Paul and Frances H. Reiff Professor of Chemistry.
In the Fall of 1986, I entered the University of Pennsylvania and worked under the guidance of Dr. William P. Dailey III. My graduate research at Penn encompassed two different areas: 1.) the synthesis and study of strained ring compounds and, 2.) the origin of the lithium perchlorate rate acceleration of the Diels-Alder reaction. In 1991, I completed my dissertation entitled “Synthetic Approaches Toward Pentaprismane, Hexaprismane, and Heptaprismane; The Lithium Perchlorate Diethyl Ether Rate Acceleration of the Diels-Alder Reaction: Lewis Acid Catalysis by Lithium Ion” and was awarded my doctoral degree.
After graduating form the University of Pennsylvania, I spent one year as a Patent Examiner at the U.S. Patent and Trademark Office in Arlington, Virginia. In August of 1992, I joined the Saint Joseph’s University Chemistry Department and was promoted to Associate Professor in 1999. Since 2010, I have been Chair and Professor of Chemistry. While at Saint Joseph’s University, I have initiated an active research program involving undergraduates that has been funded by grants from the Research Corporation, the American Chemical Society-Petroleum Research Fund, the Council on Undergraduate Research, and Pfizer Inc.
B.A. Franklin & Marshall College (1986)
Ph.D. University of Pennsylvania (1991)
CHM 210 Organic Chemistry I for Chemistry Majors
CHM 215 Organic Chemistry II for Chemistry Majors
CHM 210L Organic Chemistry Laboratory I for Chemistry Majors
CHM 215L Organic Chemistry Laboratory II for Chemistry Majors
CHM 430 Mechanisms in Organic Chemistry
CHM 210L Organic Chemistry Laboratory I
CHM 215L Organic Chemistry Laboratory II
Mark A. Forman,* Caitlin Moran, Joseph P. Herres , Jason Stairs, Emily Chopko, Anthony Pozzessere, Michael Kerrigan, Carisa Kelly, Lisa Lowchyj, Annemarie Gallo, Elizabeth Loutzenhiser “Generation and Reactions of Pentacyclo[4.3.0.02,4.03,8.05,7]non-4(5) ene”, J. Org Chem, 2007, 72, 2996 – 3005.
Joseph P. Herres, Mark A. Forman, Kraig A. Wheeler “11,12-Bis(2,2-dimethylpropyl)-9,10-dihydro-9,10-ethenoanthracene,” Acta Cryst. 2005, E61,o3961-o3963.
Joseph P. Herres, Mark A. Forman, Kraig A. Wheeler and Glenn P. A. Yap “11-(2,2-Dimethylpropyl)-12- 2-[12-(2,2-dimethylpropyl)-9,10-dihydro9,10-ethenoanthracen-11-yl]ethyl -9,10-dihydro-9,10ethenoanthracene,” Acta Cryst. 2005, E61, o1223-o1225.
Mark A. Forman and Brian Zanoni, “The Molecular Structure of 1-Substituted Bicyclo[2.2.0]hexanes: A Combined Ab Initio and X-Ray Structural Study,” Structural Chemistry, 1998, 9, 27.
Mark A. Forman, “Carbocyclic Cage Compounds: Laboratory Curiosities or More?,” The Chemist, 1996, 73, 3-8.
Mark A. Forman, Lisa E. Boyer, Jason Brazillo, and Brain Zanoni, “Favorskii Reactions of& a Bromo Quadricyclanone,” J. Org. Chem., 1996, 61, 7611-7613.
"Synthesis and Reactions of the [n]-prismanes. Recent Developments," Mark A. Forman and William P. Dailey, Org. Prep. Proc. Intl., 1994, 26 (3), 291-320.
"Convenient Synthesis of the 1,4-Bishomo-6-secoheptaprismane Ring System," Mark A. Forman and William P. Dailey, J. Org. Chem., 1993, 58, 1501-1507.
"The Lithium Perchlorate-Diethyl Ether Rate Acceleration of the Diels-Alder Reaction: Lewis Acid Catalysis by Lithium Ion," Mark A. Forman and William P. Dailey, J. Am. Chem. Soc. 1991, 113, 2761.
"The Thermal Rearrangement of Endo-7-methyl-exo-7-vinylbicyclo[3.2.0]Hept-2-ene," Phyllis A. Leber and Mark A. Forman, Tetrahedron Lett. 1986, 4107.
The focus of my research program involves the synthesis and study of non-natural products that possess unique properties and enhanced reactivity as a result of forced deviations from their ideal geometries. In particular, my research group has been interested in studying the effects of bond angle distortion on the structures and properties of alkenes.
An sp2 hybridized carbon atom is known to have a trigonal planar arrangement of its orbitals with the bond angle of 120o. We are interested in the synthesis and study of alkenes incorporated into rigid polycyclic systems such that a deviation from planarity is forced.
One type of distortion in alkenes is referred to as pyramidalization and results from a syn-folding of the R group substituents. The degree of folding may be conveniently measured via the pyramidalization angle, Φ, which is defined as the angle between the plane containing one of the doubly bonded carbons and the two substituents (R) attached to it and the extension of the double bond. Representative alkenes possessing pyramidalization of their double bonds include cubene (1) and pentacyclo[4.3.0.02,4.03,8.05,7]non-4,5-ene (2). My research group is currently pursuing an investigation of the synthesis and study of pentacyclo[4.3.0.02,4.03,8.05,7]non-4,5-ene (2).
Figure 1. a.) The σ and π bond of an alkene.
b.) The ideal bond angles of an alkene are 120o.
c.) The σ bond of an alkene can be represented by a line. Note that for clarity, the carbon atoms (C) are not shown.
d.) The π bond of an alkene resulting from the parallel overlap of p-orbitals above and below the σ-framework.
e.) The pyramidalization or syn-folding of a carbon-carbon double bond. The pyramidalization angle, Φ, is shown.
f.) Some representative pyramidalized alkenes.