Reaction of red phosphorus (P n ) with alkanethiolate anions

Трофимов, Б. А.; Гусарова, Н. К.; Verkhoturova, S. I.; Mikhailenko, V. L.; Kazantseva, T. I.; Arbuzova, S. N.; Kazheva, Olga N.; Александров, Г. Г.; D’yachenko, O. A.

doi:10.1134/s0012500809070052

Cited by 7 publications

(5 citation statements)

References 7 publications

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“…A few reports described the use of thiolates for activation of P red or P white in the presence of H 2 O to produce thiophosphites or thiophosphates. − Likewise, we conducted reactions with various alkyl thiolates (Table ) to evaluate their potential for activating P red under reaction conditions similar to those used with alkoxides. A mixture of P red and thiolate was heated in refluxing THF/DME (1:1 v/v).…”

Section: Resultsmentioning

confidence: 99%

Nucleophilic Activation of Red Phosphorus for Controlled Synthesis of Polyphosphides

Dragulescu‐Andrasi

Miller

et al. 2020

Inorg. Chem.

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Reactions between red phosphorus (P red ) and potassium ethoxide in various organic solvents under reflux convert this rather inert form of the element to soluble polyphosphides. The activation is hypothesized to proceed via a nucleophilic attack by ethoxide on the polymeric structure of P red , leading to disproportionation of the latter, as judged from observation of P(OEt) 3 in the reaction products. A range of solvents has been probed, revealing that different polyphosphide anions (P 7 3− , P 16 2− , P 213− , and P 5 − ) can be stabilized depending on the combination of the boiling point and dielectric constant (polarity) of the solvent. The effectiveness of activation also depends on the nature of nucleophile, with the rate of reaction between P red and KOR increasing in the order t-Bu < n-Hex < Et < Me, which is in agreement with the increasing order of nucleophilic strength. Thiolates and amides were also examined as potential activators, but the reaction with these nucleophiles were substantially slower; nonetheless, all reactions between P red and NaSR yielded exclusively P 16 2− as a soluble polyphosphide product.

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Section: Resultsmentioning

confidence: 99%

Nucleophilic Activation of Red Phosphorus for Controlled Synthesis of Polyphosphides

Dragulescu‐Andrasi

Miller

et al. 2020

Inorg. Chem.

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“…The latter are readily alkylated with organic halides to give S,S,S-trialkyl trithiophosphates (Scheme 20). 37 Thus, the discovered reactions contribute a principally new basic knowledge to the chemistry of phosphorus and open extra possibilities for synthesis of phosphorus-containing compounds from red phosphorus. 36…”

Section: Phosphorylation In the P N /Msr/dmso Systemsmentioning

confidence: 99%

Elemental phosphorus in strongly basic media as phosphorylating reagent: a dawn of halogen-free ‘green’ organophosphorus chemistry

Трофимов

Гусарова

2009

Mendeleev Communications

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“…1). In recent years, several methods have been developed for the synthesis of phosphorothioate esters [28][29][30][31][32][33][34][35][36][37] (Scheme 1). In 1951, an interaction of dialkyl disulfides with P 4 at high temperatures was reported by Stevens and coworker.…”

Section: Introductionmentioning

confidence: 99%

Direct synthesis of phosphorotrithioates from [TBA][P(SiCl₃)₂] and disulfides

Luo¹,

Li²,

Wang³

et al. 2023

Org. Biomol. Chem.

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Reaction of red phosphorus (P n ) with alkanethiolate anions

Cited by 7 publications

References 7 publications

Nucleophilic Activation of Red Phosphorus for Controlled Synthesis of Polyphosphides

Nucleophilic Activation of Red Phosphorus for Controlled Synthesis of Polyphosphides

Elemental phosphorus in strongly basic media as phosphorylating reagent: a dawn of halogen-free ‘green’ organophosphorus chemistry

Direct synthesis of phosphorotrithioates from [TBA][P(SiCl₃)₂] and disulfides

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Reaction of red phosphorus (P n ) with alkanethiolate anions

Cited by 7 publications

References 7 publications

Nucleophilic Activation of Red Phosphorus for Controlled Synthesis of Polyphosphides

Nucleophilic Activation of Red Phosphorus for Controlled Synthesis of Polyphosphides

Elemental phosphorus in strongly basic media as phosphorylating reagent: a dawn of halogen-free ‘green’ organophosphorus chemistry

Direct synthesis of phosphorotrithioates from [TBA][P(SiCl3)2] and disulfides

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Direct synthesis of phosphorotrithioates from [TBA][P(SiCl₃)₂] and disulfides