Methanephosphonate

Esters are named by prefixing the hydrocarbon radical name to the reminder of the name and replacing the ending -ic or -ous with -ate or -ite, respectively. For example, CH3P(0) (OC2H5)2 is named diethylmethylphosphonate or diethyl-methanephosphonate. 

Diethyl azidomethanephosphonate 228 reacts with norbornadiene at room temperature to give triazoline 229 in 86% yield. When heated at 60°C, derivative 229 decomposes with elimination of cyclopentadiene to provide (1,2,3-triazol-l-yl)methanephosphonate 230 in 74% yield. However, when it is left at room temperature for an extended period of time, triazoline 229 undergoes slow conversion to aziridine 231 with elimination of nitrogen (Scheme 30)... 

Diethanol Sulfide Diethanolamine Diethanolethylamine Diethanolmethylamine Diethoxyethylphosphine Oxide Diethoxymethylphosphine Oxide Diethoxyphosphine Oxide Diethyene Disulfide Diethyl Acid Phosphate Diethyl Ethanephosphonate Diethyl Ethylphosphonate Diethyl Hydrogen Phosphate Diethyl Hydrogen Phosphite Diethyl Hydrogen Phosphonate Diethyl Isopropylphosphonate Diethyl Methanephosphonate Diethyl Methylphosphonate Diethyl Phosphate Diethyl Phosphite Diethyl Phosphonate Diethyl Phosphoric Acid Diethyl(2-hydroxyethyl)amine Diethyl(/S-hydroxyethyl)amine Diethylaminoethanol Diethylethanolamine Diethylfosfit... 

Formation of the carbanion of diethyl 1-fluoro-1-(phenylsulfonyl)-methanephosphonate is followed by gas chromatography, by quenching a small aliquot of the reaction in ether/saturated aqueous ammonium chloride. The carbanion forms in ca. 85% to 95% yield after 1 hr. 

The reaction of 2,2-disubstituted 1,3-cyclohexanediones 1 with dimethyl methanephosphonate in THF in the presence of LDA gives 3-substituted 2-cyclohexenones 2 in moderate to very good yields. 

Dimethyl methanephosphonate (water contaminant) Tabun (also known as Trilon 83, nerve agent)... 

Mitchell MB, Sheinker VN, Mintz EA (1997) Adsorption and Decomposition of Dimethyl Methanephosphonate on Metal Oxides, J Phys Chem B 101 11192-11203... 

DIISOPROPYL METHYLPHOSPHONATE (Methanephosphonic acid, diisopropyl ester)... 

The reference cited [5] also gives procedures for related magnesiations of other carboxylic acids, phenylacetronitrile, t-butyl acetate, acetophenone, methyl phenyl sulfone, and diethyl phenyl-methanephosphonate. 

Cool the reaction mixture and replace the condenser with the distillation setup. Distil over the diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate, 42 (b.p. 170°C, 10 mmHg, 28.8 g, 91 mmol, 92%), as a colourless liquid. 

For desilylation in a 500 mL round-bottomed flask stir a solution of diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate 42 (28.8 g, 91 mmol) in 1 mM trifluoroacetic acid in methanol (300 mL) for 4-10 h at room temperature. The reaction may be monitored by gas chromatography (GC). 

SYNS DIPHENYL METHANEPHOSPHONATE DIPHENYL METHYLPHOSPHONATE PHOSPHONIC ACID, METHYL-, DIPHENYL ESTER SAFETY PROFILE A poison by ingestion. When heated to decomposition it emits toxic vapors of POx. 

DIPHENYL METHANEPHOSPHONATE see MDQ825 DIPHENYLMETHANONE see BCS250 2-piPHENYLMETHOXY)-N,N-DIMETHYL-ETHANAMINE HYDROCHLORIDE see BAU750 2-(DIPHENYLMETHOXY)-N,N-DIMETHYLETHYLAMINE see BBV500... 

METHANE DICHLORIDE see MJP450 METHANEDITHIOL-S,S-DIESTER with 0,0-DIETHYL ESTER PHOSPHORODITHIOIC ACID see EEH600 METHANE, PHENYL- see TGK750 METHANEPHOSPHONIC ACID, DIPHENYL ESTER see MDQ825... 

Chiral vinyl sulfoxides have been prepared by a Wittig Horner reaction of chiral (R)- or (.Si-dimethyl (4-tolylsulfinyl)methanephosphonate with carbonyl compounds3-66,67. For acyclic systems reprotonation of the anions from vinyl sulfoxides gave a mixture of E- and Z-isomers3, whereas isomerization of an exocyclic double bond in a ring system provided access to chiral aryl 1-cycloalkenylmethyl sulfoxides66-67. 

A synthetic procedure has been developed which enables the (Rp)-diastereoisomer of dinucleoside methanephosphonates to be prepared in up to 79% diastereomeric excess.Reaction of dichloromethylphosphine with the 3 -hydroxy function of an otherwise protected nucleoside at -80 C gives the chloromethylphosphlne (81) as a 1 1 mixture of dlastereoisomers as determined by n.m.r. Stereochemical induction therefore occurs in the subsequent... 

The formation of a triple-helix with dA19.dT19.dT19 has been studied in which one of the homo-pyrimidine oligodeoxyrlbonucleotlde strands is replaced with the analogous strand containing all methanephosphonate linkages.In contrast to a previous report there was no evidence for triple-helix formation. 

The glycoside 260 is converted into the cyclopentenone 261 on reaction with dimethyl methanephosphonate and base [210] (O Scheme 56). The tandem -fragmentation-cycloisomerization of the unsaturated lactol 262 gives the carbocycle 263 [211]. 

Precursors to thymidine-3 -0-(S-aryl methanephosphothionate) (50) have been prepared and treated with triphenylphosphine to provide access to novel dinucleotide 3, 5 -methanephosphonate analogues (Scheme 3). The reaction of... 

Coutrot, P, Youssefi-Tabrizi, M., and Grison, C.. Diethyl-1-magnesium chloride methanephosphonate. a novel Grignai d reagent and its use in organic synthesis, 7. Organomet. Chem.. 316, 13, 1986. 

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