Date Approved

2013

Degree Type

Open Access Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Committee Member

Donald Snyder

Committee Member

Timothy Brewer

Committee Member

Gregg Wilmes

Abstract

Amino bisphosphonate compounds are found in a vast array of products from water chelators to flame retardants to pharmaceuticals. Previous methods to synthesize these compounds involved the use of protic acids, which don’t provide ideal conditions for the starting materials containing acid labile functional groups in pharmaceutical compounds. The present study adopts a new synthetic route in which diethyl phosphite addition to the nitrile would be effected in the presence of a Lewis acid catalyst. This study utilized lanthanum trifluoromethane sulfonate as the Lewis acid catalyst, facilitating the addition of the P-H bond across the nitrile triple bond. Product purification by short path distillation provided 90% pure product for the reaction with benzonitrile in 27% yield (structure was confirmed by 1H and 13C NMR), although purification by column chromatography was ineffective. Formation of the addition products in the remaining reactions was presumed on the basis of TLC results.

Included in

Chemistry Commons

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