2014
DOI: 10.14233/ajchem.2014.16607
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Synthesis and Crystal Structure of Diethyl Tosyloxybenzylphosphonate

Abstract: Diethyl tosyloxybenzylphosphonate was synthesized by the reaction of hydroxybenzylphosphonate with p-toluenesulfonyl chloride characterized by NMR spectroscopy, elemental analyses and X-ray single-crystal diffraction. The possessing parameters: m.f. C18H23O6PS,

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Cited by 5 publications
(8 citation statements)
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“…: 63−64 °C, mp lit. : 29 6.5. General Procedure for the Synthesis of Diethyl α-Chloro-arylphosphonates.…”
Section: Dimethyl α-Methanesulfonyloxy-benzylphosphonate (4a)mentioning
confidence: 99%
See 1 more Smart Citation
“…: 63−64 °C, mp lit. : 29 6.5. General Procedure for the Synthesis of Diethyl α-Chloro-arylphosphonates.…”
Section: Dimethyl α-Methanesulfonyloxy-benzylphosphonate (4a)mentioning
confidence: 99%
“…A simple, but relatively less studied modification is alkylation . A much better-studied reaction is their acylation. This change in the functionality was especially useful in making available biologically active species. The phosphorylation of hydroxyphosphonates was elaborated by us. , At first sight, it may be seen as surprising that the α-hydroxy-benzylphosphonates underwent substitution with primary amines on microwave (MW) irradiation. , The reaction was promoted by an adjacent group effect. Additional transformations of α-hydroxyphosphonates include rearrangement, , dealkylation, and oxidation and reduction .…”
Section: Introductionmentioning
confidence: 99%
“…Besides carboxylic chlorides, anhydrides and acids, sulfonic acid derivatives may also function as the acylating agents. By analogy with the reaction of α-hydroxyphosphonates ( 1B ) with carboxylic chlorides, the acylation was also attempted with sulfonyl chlorides [ 95 , 96 , 97 ]. Methanesulfonyl chloride ( Scheme 14 , Route “a”) [ 96 ] and p -toluenesulfonyl chloride ( Scheme 14 , Route “b”) [ 97 ] worked well as sulfonylating agents in the presence of triethylamine.…”
Section: Reactions Of α-Hydroxyphosphonatesmentioning
confidence: 99%
“…Beyond their potential bioactivity, the α-hydroxyphosphonates may be important intermediates in a series of syntheses [ 1 ]. The most important reactions are alkylations [ 1 ], acylations [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ], phosphorylations [ 28 ], substitutions [ 1 ], rearrangements [ 1 ], and dealkylations [ 1 ]. As regards acylations, a series of α-(aryloxyacetoxy)-alkylphosphonate derivatives [ 12 , 13 , 14 , 15 ] was prepared mainly by acylation of different α-hydroxyphosphonates with carboxylic acid chlorides, including aryloxy-butyryloxy or -valeroxy [ 16 ] and heterocyclic derivatives [ 17 , 18 ].…”
Section: Introductionmentioning
confidence: 99%
“…Obviously, this is an elegant way of acylation. It is noteworthy that a tosyloxybenzylphosphonate was also described [ 27 ]. The phosphorylation of α-hydroxyphosphonates [ 28 ] was elaborated by us.…”
Section: Introductionmentioning
confidence: 99%