Synthesis and characterization of decyl phosphonic acid, applications in emulsion polymerization and anti-corrosion coating

Phan, The-Anh; Perrin, F.X.; Nguyen-Dinh, Lam

doi:10.1007/s11814-018-0041-9

Cited by 4 publications

(2 citation statements)

References 27 publications

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“…[14,[49][50][51] Diethyl undecylphosphonate 10 a is a novel compound, but readily accessible via Michaelis-Arbuzov coupling of triethyl phosphite and undecyl bromide with a yield of 79 %. [52][53][54] Chlorination of this compound with Scheme 1. Overview of commonly used methodologies for the synthesis of phosphonamidate moieties.…”

Section: Resultsmentioning

confidence: 99%

“…Convinced by the application potential of these phosphonylaminium salts, we chose to compare pyridine and triethylamine as mediators for the synthesis of phosphonamidates using diethyl undecylphosphonate and isopropylamine as model substrates (Scheme 2). [14,49–51] Diethyl undecylphosphonate 10 a is a novel compound, but readily accessible via Michaelis–Arbuzov coupling of triethyl phosphite and undecyl bromide with a yield of 79 % [52–54] . Chlorination of this compound with oxalyl chloride at room temperature delivered the monochloride in sufficient purity to be directly used in the next step.…”

Section: Resultsmentioning

confidence: 99%

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Triethylamine‐Mediated Transformation of Phosphonates into Phosphonamidates

Backx,

Dejaegere,

Simoens

et al. 2023

Eur J Org Chem

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Organophosphorus compounds such as phosphonamidates are gaining attention across different fields of chemistry, with interesting applications as pharmaceuticals, or pesticides. However, practical application of phosphonamidates is complicated by their difficult syntheses which often involve expensive or unstraightforward reagents and harsh conditions. To remedy these issues, we present a flexible, room temperature synthesis for novel P‐alkylphosphonamidates without the need for intermediary purification. Commonly available phosphonates are first chlorinated by use of oxalyl chloride and phosphonylaminium salts are used to mediate the harsh reactivity of phosphonochloridates, giving rise to the desired products. We demonstrate the compatibility of our protocol with primary and secondary amines, as well as with different phosphonate esters. The proposed pathway also enables the synthesis of primary phosphonamidates using ammonium acetate as a cheap and safe alternative for ammonia. In future research, this protocol will also enable the synthesis of bioactive targets that are incompatible with current protocols.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Triethylamine‐Mediated Transformation of Phosphonates into Phosphonamidates

Backx,

Dejaegere,

Simoens

et al. 2023

Eur J Org Chem

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Synthesis of Long‐Chain n‐Alkylphosphonic Acids by Phosphonylation of Alkyl Bromides with Red Phosphorus and Superbase under Micellar/Phase Transfer Catalysis

et al. 2021

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Long‐chain n‐Alkylphosphonic acids, AlkP(O)(OH)2, are synthesized in up to 91 % yield (mostly 40–60 %) by straightforward phosphonylation of alkyl bromides (AlkBr, Alk=C4–C18) with red phosphorus (Pn) in the multiphase KOH/H2O/toluene system in the presence of 2–10 mol % of cetyltrimethylammonium bromide (CTAB), acting as a micellar/phase transfer catalyst and as a generator/transporter of superbasic hydroxide anions, the intermediate potassium phosphinates being in situ oxidized/neutralized by nitric acid. The key steps of the phosphonylation mechanism are the P−P bond cleavage of Pn polymeric molecules by superbasic −OH anions, dissolved in the CTAB micelles, and phase transfer of polyphosphide anions to the organic phase and their alkylation with AlkBr.

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