Organophosphorus compounds. P-Arylated perhydro-1,2-azaphosphorines

Abstract

Treatment of ethyl 4-bromobutylphosphonochloridate with phenylmagnesium bromide, followed by acid-catalysed hydrolysis of the product, gave 4- bromobutyl(phenyl)phosphinic acid. This was converted into the corresponding phosphinamide by treatment with thionyl chloride and then with aqueous ammonia. Cyclodehydrobromination with sodium hydride in warm xylene then gave a good yield of 2-phenylperhydro-1,2- azaphosphorine 2-oxide. Some other routes to this compound were investigated.

Synthesis of a New Series of Phosphonylated 1,2,3‐Triazoles as Acyclic Analogs of Ribavirin

“…The starting azidophosphonates 12a , 12b , 12c , 12d , 12e , 12f , 12g , and 12h are known and were prepared according to the literature methods except for 12a , since the existing methods for the synthesis of this compound are rather discouraging in terms of application of highly toxic hydrazoic acid and lack of commercial availability of tetramethylguanidinium azide . Our experience with in situ generated ammonium azides prompted us to apply this approach also in the synthesis of 12a via displacement of a nosyl group (Scheme ).…”

Facile synthesis of phosphorylated azides in ionic liquids and their use in the preparation of 1,2,3‐triazoles

“…The starting ω-bromoalkylphosphonates 1a-c were obtained via an Arbuzov reaction of the corresponding α,ω-dihalogenoalkanes with triethylphosphite according to [29], [30] and [31] for n = 2, 3, and 4, respectively. Propargyl-substituted fluorinated alcohol 3d and protected amino acids 3f,e were obtained via the processes reported by one of us previously, based on the Grignard reagent addition to high-electrophilic methyl trifluoropyruvate and its imines [27].…”

Design, cytotoxic and fluorescent properties of novel N-phosphorylalkyl substituted E,E-3,5-bis(arylidene)piperid-4-ones

“…The starting diethoxy(3-bromopropyl)phosphonate [33] and diethoxy(4-bromobutyl)phosphonate [34] were obtained by the Arbuzov reaction of triethylphosphite and 1,3-dibromopropane or 1,4-dibromobutane correspondingly according to the known procedures. Other reactants were purchased from Aldrich and used without further purification.…”