Master's Theses

Document Type

Thesis - campus only access

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.


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Copyright 1967 Ronald Louis Horinek

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