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Phosphite esters may be used as reducing agents in more specialised cases. For example, triethylphosphite is known to reduce certain hydroperoxides to alcohols formed by autoxidation [7] (scheme). In this process the phosphite is converted to a phosphate ester. This reaction type is also utilized in the Wender Taxol total synthesis.
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.
When aliphatic alcohols are used the HCl by-product can react with the phosphate esters to give organochlorides and a lower ester. O=P(OR) 3 + HCl → O=P(OR) 2 OH + RCl. This reaction is usually undesirable and is exacerbated by high reaction temperatures. It can be inhibited by the use of a base or the removal of HCl through sparging.
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The Buchner–Curtius–Schlotterbeck reaction is the reaction of aldehydes or ketones with aliphatic diazoalkanes to form homologated ketones. [1] It was first described by Eduard Buchner and Theodor Curtius in 1885 [2] and later by Fritz Schlotterbeck in 1907. [3]
Technically there are other ketone esters such as acetoacetate bound to D/L 1,3-butanediol (racemic). This diester has been tested more with deep sea divers. It is not commercially available. [10] Another ketone ester is also referred to as a ketone di-ester which is a bond of C6 and R 1,3 butanediol or C8 and R 1,3 butanediol.
Diethyl phosphite hydrolyzes to give phosphorous acid. Hydrogen chloride accelerates this conversion.: [2] Diethyl phosphite undergoes transesterification upon treating with an alcohol. For alcohols of high boiling points, the conversion can be driven by removal of ethanol: [8] (C 2 H 5 O) 2 P(O)H + 2 ROH → (RO) 2 P(O)H + 2 C 2 H 5 OH
Triethyl phosphite (TEP) is an organophosphorus compound, specifically a phosphite ester, with the formula P(OCH 2 CH 3) 3, often abbreviated P(OEt) 3. It is a colorless, malodorous liquid. It is used as a ligand in organometallic chemistry and as a reagent in organic synthesis.