Abstract
M.Sc. (Chemistry)
The work in this thesis describes some catalytic reactions of aluminium triflate. This Lewis acid
has been shown to be of great value in the catalysis of several types of organic transformations.
These include but are not limited to the alcoholysis and aminolysis of epoxides, uses in
methoxycarbonylation catalysis and in esterification reactions. Therefore, aluminium triflate
holds promise for application in both the bulk and fine chemistry industries. Aluminium triflate
has received little interest compared to some other, more costly triflates such the lanthanide
triflates.
Oxetanes were used in various catalysis experiments during this study, yet few are commercially
available. Therefore, various synthetic approaches to the synthesis of 2-phenyl-oxetane were
explored. There were many failed attempts, but the preparation was eventually successful using a
sulfur ylide route with good yield.
The next part of this thesis explores the boundaries of ring-opening reactions of oxetanes. Lewis
acid ring-opening of oxetanes has been neglected compared to that of epoxides, likely because it
is a more difficult undertaking. Yet, alcoholysis reactions showed good yields with a variety of
different alcohol substrates. Some of the alcohols contained functionality which could provide
access to further modification. Furthermore, the aminolysis and thiolysis of oxetanes were
explored, essentially without success. However, with an activated oxetane it was shown that
oxetanes could be opened with good yield under mild conditions with amines and thiols...