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The general structure of a phosphite ester showing the lone pairs on the P. In organic chemistry, a phosphite ester or organophosphite usually refers to an organophosphorous compound with the formula P(OR) 3. They can be considered as esters of an unobserved tautomer phosphorous acid, H 3 PO 3, with the simplest example being trimethylphosphite ...
The nerve gas agent sarin, containing both C–P and F–P bonds, is a phosphonate. [citation needed] Phosphinates feature two P–C bonds, with the general formula R 2 P(=O)(OR'). A commercially significant member is the herbicide glufosinate. Similar to glyphosate mentioned above, it has the structure CH 3 P(O)(OH)CH 2 CH 2 CH(NH 2)CO 2 H.
The wide variety of substitutes used in organophosphate esters results in great variations in physical properties. OPEs exhibit a wide range of octanol/water partition coefficients where log Kow values range from -0.98 up to 10.6. [5] Mono- and di- esters are usually water soluble, particularity biomolecules.
An ester of carboxylic acid.R stands for any group (organic or inorganic) and R′ stands for organyl group.. In chemistry, an ester is a compound derived from an acid (organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group (−OH) of that acid is replaced by an organyl group (−R).
The phosphite esters and tertiary phosphines also effect reduction: ROOH + PR 3 → P(OR) 3 + ROH. Cleavage to ketones and alcohols occurs in the base-catalyzed Kornblum–DeLaMare rearrangement, which involves the breaking of bonds within peroxides to form these products.
Phosphonites are generally more reactive than phosphite esters. They react to produce phosphinates. Heating is also required for the reaction, but pyrolysis of the ester to an acid is a common side reaction. The poor availability of substituted phosphonites limits the usage of this class of reagent in the Arbuzov reaction.
Phosphines have also been found to reduce activated carbonyl groups, for instance the reduction of an α-keto ester to an α-hydroxy ester in scheme 2. [13] In the proposed reaction mechanism , the first proton is on loan from the methyl group in trimethylphosphine (triphenylphosphine does not react).
Diethyl phosphite is the organophosphorus compound with the formula (C 2 H 5 O) 2 P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond.