meeting follow up

2003 Milwaukee Section Award Reactivity Characteristics of Spiroactivated Clyclpropanes Michael A. McKinney Dean, College of Letters and Sciences Professor of Chemistry Marquette University

Friday November 14, 2003 Lunda Room, Alumni Memorial Union Marquette University

DIRECTIONS

Over the past three decades, research in my laboratory has encompassed the broad field of physical organic chemistry. Of particular interest has been the unusually high reactivity of spirocyclic donor-acceptor cyclopropyl systems. When the spirocyclic substituents are electron withdrawing groups, ring opening reactions include thermal rearrangement and solvolytic (nucleophilic) cleavage. Kinetic measurements are used to determine reaction order as well as the effects of solvent polarity and donor characteristics on the rates of ring cleavage. Reaction stereochemistry is determined utilizing deuterium labeling and chiral substrates. X-ray crystal analysis of a series of spirocyclic systems has shed light on the nature of the initial state cyclopropyl bond asymmetries which helps explain the regiochemistry of reaction as well as reactivity characteristics.

When the spirocyclic substituents are donor groups, the cyclopropyl ring enters into [3+2] cycloaddition reactions with dienophiles. Unlike the Diels-Alder reaction which is concerted, we find this cycloaddition proceeds stepwise through a zwitterionic intermediate which was trapped with the aid of an appropriately designed dieneophile.

A survey of the mechanisms elucidated will be presented focusing on the wide range of physical organic techniques utilized in these studies.

Michael A. McKinney, professor of Chemistry, is Dean of the College of Arts and Sciences at Marquette University. Reporting to the Provost, the Dean of the oldest and largest college of Marquette University provides leadership for the chairpersons of twelve academic departments and the co-directors of the University Honors Program.

Prior to assuming his present position, McKinney was chair (for eleven years) and a faculty member in the Department of Chemistry at Marquette since 1967. In 1997, he received the Faculty Award for Teaching Excellence and in 1998 he was inducted as an honorary member of Alpha Sigma Nu, the Jesuit Honor Society. The Chemistry seniors awarded him the Senior Award in 1986, 1988, and 1989, in recognition of teaching excellence and developmental guidance of future scientists.

McKinney has published numerous articles in scholarly journals in the fields of physical organic chemistry and most recently, through collaboration with Charles Wilkie, flame-retardation. He has formally mentored over forty undergraduates in his research laboratory and served as director for fourteen masters degree and eight doctoral degree recipients. His research has been supported individually or in collaboration by grants from the National Institute of Health, the Petroleum Research Fund of the American Chemical Society, and the National Institute of Standards and Technology. Corporation support for undergraduate student research includes awards from S.C. Johnson Wax and G.D. Searle-Nutrisweet. McKinney has also secured instrumentation and training grants from the National Science Foundation, the Camille and Henry Dreyfus Foundation and the Department of Education. He has been an active member of the American Chemical Society (ACS) serving on the National Organic Chemistry Exam Committee for twenty years and as chairperson of the Milwaukee Section of the ACS in 1996-1997. During his terms as chair of the Department of Chemistry and now as Dean, he is a member of the Council for Chemical Research, a national organization founded in 1979 to promote cooperation between industry, academia, and government in basic research and to encourage quality education in the chemical sciences and engineering.

McKinney earned his bachelor's degree at Loyola University, Chicago, in 1961 and his Ph.D. at the Illinois Institute of Technology in 1966, where he was a U.S. Steel Foundation Fellow. Supported by a National Science Foundation Fellowship, he held a one-year postdoctoral appointment at Yale University just prior to his arrival at Marquette. He has lectured extensively both nationally and internationally at universities and scientific conferences. McKinney has held visiting professorship appointments at the University of Toronto, Northwestern University and University College Dublin.

At the meeting were a number of previous Milwaukee Section Award recipients. These are shown below. Also in attendance were there members who were being honored as being a member of the ACS for 50 years.

Mike receives his award from Steve Levsen	50 year ACS members (l-r) Roger Senn, Frank DiPierro and Kenneth Hamm
Milwaukee Section Award Winners who were attending the celebration at the November meeting. (l-r) Dimitri Gorjestani (1988), Kazuo Nakamoto (1979), James Kincaid (1998), Glenn Svoboda (1978), Stan Flashinski (1995), Steve Levsen, Charles Wilkeie (1992) and Dan Bloch (1990).