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.
","abstract_html":"<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>","abstract_has_math":false,"creators":["Vanja, Prasanna"],"institution":null,"degree_name":"Master of Science (MS)","degree_level":"Open Access Thesis","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Donald Snyder","Timothy Brewer","Gregg Wilmes"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2013,"date_issued":"2013-01-01T08:00:00Z","date_published":"2013-01-01T08:00:00Z","updated_at":"2026-07-24T02:17:27Z","subjects":["1-aminoalkyl-1","1-diphosphonic acid","AminoBisphosphonates","Diethyl Phosphite","Flame Retardants","Lanthanum Catalyst","Nitrile with Phosphite","Chemistry","Physical Sciences and Mathematics"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://commons.emich.edu/theses/882","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Donald Snyder","Timothy Brewer","Gregg Wilmes"]},{"key":"dc:creator","label":"Author","values":["Vanja, Prasanna"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2018-03-15T07:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Open Access Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (MS)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["1-aminoalkyl-1","1-diphosphonic acid","AminoBisphosphonates","Diethyl Phosphite","Flame Retardants","Lanthanum Catalyst","Nitrile with Phosphite","Chemistry","Physical Sciences and Mathematics"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://commons.emich.edu/theses/882"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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.
"]},{"key":"dc:title","label":"Title","values":["Study of the reaction of nitriles with dialkyl phosphites for synthesis of a-Amino-bis-phosphonates"]}]}],"canonical_facts":{"dc:contributor":["Donald Snyder","Timothy Brewer","Gregg Wilmes"],"dc:creator":["Vanja, Prasanna"],"dc:date.available":["2018-03-15T07:00:00Z"],"dc:description.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.
"],"dc:identifier":["https://commons.emich.edu/theses/882"],"dc:subject":["1-aminoalkyl-1","1-diphosphonic acid","AminoBisphosphonates","Diethyl Phosphite","Flame Retardants","Lanthanum Catalyst","Nitrile with Phosphite","Chemistry","Physical Sciences and Mathematics"],"dc:title":["Study of the reaction of nitriles with dialkyl phosphites for synthesis of a-Amino-bis-phosphonates"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Open Access Thesis"],"thesis:degree_name":["Master of Science (MS)"]},"updated_at":"2026-07-24T02:17:27Z"}