Study of the reaction of nitriles with dialkyl phosphites for synthesis of a-Amino-bis-phosphonates

<p>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.</p>

Name thesis:degree_name

Master of Science (MS)

Level thesis:degree_level

Open Access Thesis

Discipline thesis:degree_discipline

Chemistry

Year dc:date.available

2013

Author dc:creator

• Vanja, Prasanna

Contributors dc:contributor

• Donald Snyder
• Timothy Brewer
• Gregg Wilmes

• 1-aminoalkyl-1
• 1-diphosphonic acid
• AminoBisphosphonates
• Diethyl Phosphite
• Flame Retardants
• Lanthanum Catalyst
• Nitrile with Phosphite
• Chemistry
• Physical Sciences and Mathematics

Repository record dc:identifier

https://commons.emich.edu/theses/882

OAI identifier oai:identifier

oai:commons.emich.edu:theses-2262