Master's Theses

Off-campus FHSU users: Please use the following link to log into our proxy server and download this work.

Date of Award

Spring 1967

Degree Name

Master of Science (MS)




James H. MeMechan


Two methods for the preparation of [gamma]-pyronocoumarins have been performed; the ring closure of an o- hydroxy- [beta] - ketoacetylcoumarln and the Kostanecki-Robinson reaction of an o-hydroxy-acetylcoumarln. The [beta] - ketoacetyl route was the desired route. The use of dimethylsulfoxide in the Claisen condensation and the Baker-Venkataraman rearrangement offered a convenient method for the cinnamoyl and [beta] - diketo derivative syntheses. The [alpha] -pyrone ring of the coumarin was found to be stable in the basic dimethylsulfoxide media which was used for the rearrangement and condensation. Under other mild, basic conditions, the [alpha] -pyrone ring exhibited the same stability. A brief study was made of the C- acetylation of phenols and hydroxycoumarins with acetic anhydride catalyzed by boron trifluoride.


Copyright 1967 Ronald Louis Horinek


Notice: This material may be protected by copyright law (Title 17 U.S. Code).