o-Hydroxyaryl diphosphonic acids

Dhawan, Balram; Redmore, Derek

doi:10.1021/jo00195a029

Cited by 90 publications

(51 citation statements)

References 6 publications

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“…t ‐Butyl α‐bromomethacrylate (TBBr), diethyl (2‐hydroxyphenyl) phosphonate, and tetraethyl(2,5‐dihydroxy‐1,4‐phenylene)bisphosphonate were prepared according to literature procedures 26–29. The photoinitiator, 2,2‐dimethoxy‐2‐phenylacetophenone, was obtained from Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and photopolymerization of new dental monomers from o‐hydroxyaryl phosphonates

Sahin

Albayrak

Sarayli

et al. 2006

J. Polym. Sci. A Polym. Chem.

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Novel aromatic mono‐ and diphosphonate monomers based on t‐butyl α‐bromomethacrylate were prepared for use in dental composites. The synthesis of the two monomers involved three steps: the reaction of diethyl phosphite with phenol or hydroquinone, the rearrangement of the resulting phosphate derivatives into o‐hydroxyaryl phosphonates with lithium diisopropylamide, and the reaction of o‐hydroxyaryl phosphonates with t‐butyl α‐bromomethacrylate. Then, the selective hydrolysis of the t‐butyl ester groups of the monomers with trifluoroacetic acid gave the other carboxylic acid containing monomers. The photopolymerization behaviors of the synthesized monomers with glycerol dimethacrylate and triethylene glycol dimethacrylate were investigated with photodifferential scanning calorimetry at 40 °C with 2,2′‐dimethoxy‐2‐phenyl acetophenone as the photoinitiator. The hydrolysis of the t‐butyl groups of the monomers increased the reactivity and the rates of polymerization of the monomers. The mixtures of the acid monomers showed rates of polymerizations similar to those of homopolymerizations of triethylene glycol dimethacrylate and glycerol dimethacrylate. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 6775–6781, 2006

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Section: Methodsmentioning

confidence: 99%

Synthesis and photopolymerization of new dental monomers from o‐hydroxyaryl phosphonates

Sahin

Albayrak

Sarayli

et al. 2006

J. Polym. Sci. A Polym. Chem.

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“…Alternatively, tetrakis(trimethylsilyl) esters can be obtained by using chlorotrimethylsilane with sodium iodide [69]. Tetrakis(trimethylsilyl) esters were solvolyzed by alcohol or water under mild conditions (Scheme 7).…”

Section: Dealkylation Of Esters By Me 3 Sixmentioning

confidence: 99%

Synthesis of 1-hydroxy-1,1-bisphosphonates

Lecouvey

Leroux

2000

Heteroatom Chem.

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“…Diethyl chlorophosphate (4 mmol) was added to a solution of phosphonate 3 (4 mmol) and triethylamine (4 mmol) in 10 mL of benzene. The mixture was left at room temperature for 48 hours, and the precipitate that had formed was filtered off.…”

Section: Diethyl4-diethoxyphosphovyl-3-pyridyl Phosphate (4)mentioning

confidence: 99%