2-ethyl phenylphosphonic-acid

Johnson, M.K., Read, D.J. (1987). The influence of chirality on the delayed neuropathic potential of some organophosphoms esters neuropathic and prophylactic effects of stereoisomeric esters of ethyl phenylphosphonic acid (EPN oxon and EPN) correlate with quantities of aged and imaged neuropathy target esterase in vivo. Toxicol. Appl. Pharmacol. 90 103-15. 

N -butylphosphonic acid, phenylphosphonic acid, ethyl methylphosphonic acid, ethyl methylthiophosphonic acid, isopropyl methylphosphonic acid, pinacolyl methylphosphonic acid, dimethyl phenylphosphonate in 16 min Methylphosphonic acid, ethylphosphonic acid, CZE... 

Phenylphosphonic acid (1.58 g, 10 mmol) is added to a diluted solution of 40% tetrabutylammonium hydroxide (13 mL, 20 mmol) in water (100 mL) then a solution of H2W2O11 (21 mL, 20 mmol of tungsten), prepared as above, is added dropwise to the clear solution. The flaky solid that forms is collected, rinsed with cold water, and dried under vacuum at 40°C (heating above 60°C may induce decomposition of the peroxo salt). Yield 7.23 g (62%). An analytical sample was recrystallized from a mixture of 1,2-dichloroethane and ethyl acetate. 

The phosphonyl adduct 300 reacted with a dilute solution of anhydrous hydrogen chloride in ethanol or with sodium ethoxide to afford an essentially quantitative yield of the P-N cleaved product 304 with inversion of configuration. Addition of sodium ethoxide to a solution of 304 in methanol resulted in the formation of enantiomerically pure (+)-(.V)-ethyl methyl phenylphosphonate (305). It also reacted quantitatively with methylmagnesium iodide at room temperature to give the product of P-S bond cleavage 306, which upon acid catalyzed methanolysis afforded enantiomerically pure (+)-(R)- methyl methylphenylphosphinate (307) (Scheme 72) [108],... 

C2Hs)3P,(n-C,H2)3P, (CeHs)zP [(CH3)2N]3P Phosphinic acid amides Phenyl phosphorodi-(1-imidazolidate) Phosphazo compounds Trichlorophosphazo-sulfonyl compounds Phenylphosphonic dichloride 1 -Ethyl-3-methyl-3-phospholine 1-oxide P2OS... 

Vinylphosphonic acid and its ethyl ester can be obtained directly from the chloride (6.274). Diallyl phenylphosphonate is obtainable by (6.275). 

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