We have a number of projects in synthetic chemistry that are
suitable, at various stages, for students of any standing from
beginning freshmen to seniors. Brief descriptions of some of the
projects that are available follow. Much more detail on some of
the phosporus chemistry projects can be found in current proposals
that can be accessed (on-campus access only) by clicking
We are currently working on a diverse group of projects, some
of which are described below. I will be glad to personally discuss
the research with you in more detail if you so desire. If you're
interested, you may stop by my office (Nobel 303A) for discussion
of the possibilities. A call or e-mail ahead to make sure that
I will be available is a good idea; my office telephone number
is 933-7310; my e-mail address is firstname.lastname@example.org
Beginning students will usually be assigned to work on organic
synthesis projects that aim to produce intermediate compounds
for more advanced projects. Such projects serve not only to further
the research effort - they also constitute an excellent method
for learning of spectroscopy [nuclear magnetic resonance (NMR),
infrared (IR)], methods for handling sensitive materials with
exclusion of atmospheric moisture and oxygen (glove box and Schlenk
apparatus), and mechanistic and structural organic chemistry.
Inorganic synthesis projects are also available - for instance,
the preparation of transition metal coordination compounds for
further use in the more advanced projects. A good example of this
is the preparation of ethylene(bis-triphenylphosphine) platinum(0)
[formula: (Ph3P)2Pt(C2H4)] by a five-step sequence that begins
with metallic platinum.
Another aspect of synthesis in which we have an interest is in
development of new experiments for the Organic and Inorganic courses.
One such experiment, titled "Simple Preparation and NMR Analysis
of mer and fac Isomers of Tris(1,1,1-trifluoro-2,4-pentanedionato)cobalt(III):
An Experiment for the Inorganic Chemistry Laboratory," appeared
in the July 2001 issue of the Journal
of Chemical Education. Much of the research on development
of this experiment was done by Ashley Jensen, a current
Gustavus senior and coauthor of the paper. There is at present
a need for student researchers to work on experiments on synthesis
of chiral coordination complexes, chemistry of n-butylferrocene,
and isolation and NMR and IR analysis of natural products.
An alternative view of the nature of our research projects can
be heard if you discuss them with the students who are currently
working on them. Current research students' names are listed under
A poster presentation on recent developments in our acylphosphine
chemistry, given on November 6, 1999 by Ryan
Nelson at the National Meeting of Sigma Xi, the Scientific
Research Society, is on display outside of Nobel 304.
A presentation on further research on acylphosphine chemistry
was given at the 219th American Chemical Society meeting in San
Francisco, March 26- 30, by Ryan
Jeffrey Johnson. For the presentation abstract, click on the
highlighted link: our
paper was #112 .
on this work has been published in Organometallics
Philip Sass will be making a research presentation at
the 222nd American Chemical Society meeting in Chicago in August
2001. The title is "Preparation of Primary Alkylphosphines
by a Phospha-Gabriel Route". Coauthors on the paper are Jeffrey
Johnson, Ryan Nelson, and Brian O'Brien.
To view a list of projects in addition to those described on
this page, click here.
[Philip Sass (Spring & Summer 2001), Ryan
Nelson (June 2000 graduate),
Johnson (June 2000 graduate)]
Investigations in one main general area in which we are working
encompass three areas of phosphorus chemistry. The first two sub-areas
are related: we are investigating two different methods for construction
of organic phosphorus-containing molecules in such a way as to
electronically tune the back-bonding ability (i.e. cause the d
orbitals of the phosphorus atom to interact with appropriate metal
orbitals). The third area deals with compounds in which phosphorus
is connected to other atoms through double or triple bonds; compounds
of this nature are recent discoveries, so much of their chemistry
is unexplored. n the general area of phosphorus chemistry
are of interest because metal-phosphorus compounds are important
as tools for the synthesis of organic molecules which have both
biological and industrial importance; in addition, main-group
compounds of phosphorus are of current interest in the development
of new syntheses of semiconducting and photovoltaic materials.
Students who do research in the phosphorus chemistry projects
learn laboratory techniques to which they might not otherwise
be exposed, such as vacuum-line manipulation of gases, work at
low temperatures, and work under oxygen-free conditions (glove
box or Schlenk line operations) with compounds which are highly
air-sensitive. Extensive use of multinuclear NMR spectroscopy
(so far including 31P, 19F, 1H,
13C, and 119Sn NMR) is also necessary for
the analysis of the compounds with which we work. A considerable
amount of organic synthesis is also required for construction
of the organic backbones of the phosphorus-containing molecules.
Osmium, Rhenium, and Ruthenium Chemistry [no current
Students in our group have prepared and characterized a unique
compound in which osmium is bound simultaneously to four nitrogen
atoms and an oxygen atom. Current work is focused on a new and
improved method for preparation of the diamine that is used in
the synthesis, and investigation of further coordination chemistry
of the diamine and ligands prepared from it. The chemistry
associated with this project is of importance in the understanding
of the reactions of Os(VIII) compounds with organic compounds,
which, in turn, is of practical importance in organic synthesis.
A project to expand this chemistry to include other high-valent
transition metal comounds will be initiated in the near future.
tert-Alkylation of Aromatic Substrates through Friedel-Crafts
[Christopher Krug (June 2001 graduate); Donald Berkholz
(Spring 2001 & Fall 2001)]
This project is an exploration of the effects on the regioselectivity
of alkylation of acenaphthene, catalyzed by various Lewis acids.
Solvent effects are also under study. The ultimate goal of the
project is preparation of variously substituted naphthalic anhydrides
by oxidation of t-alkylated acenaphthenes.
Preparation of 4-(2-aminoethoxy)phenytoin [no
We hope to design a synthesis of this analog of phenytoin, a drug
for the treatment of Parkinson's-Disease, for use in affinity
chromatography. This is a collaborative project with John Lammert
and his students in the Gustavus Adolphus Biology department.
Friedel-Crafts Cyclialkyaltion of Phenol [no current
We are preparing cyclialkylated products of phenol so as to
elucidate the structures of the products that are formed under
conditions of catalytic oxidation.
Chemistry of Buckminsterfullerene [John Zupancich]
One of the most spectacular and intriguing chemical discoveries
ever made is the very recent discovery of a new allotrope of carbon.
The two previously known allotropes are diamond, which is a covalent
network solid, and graphite, which has a layer structure. The
new, third allotrope contains 60 carbon atoms bonded into a spherical
shape which has the same geometry as that of a soccer ball. The
new allotrope, called buckminsterfullerene due to its resemblance
to a geodesic dome, can be made simply by striking an electric
arc between graphite electrodes in an atmosphere of helium.