ChemInform Abstract: Reaction of Some PH‐Acids with Dimethylformamide Diethyl Acetal.

Abstract

Reaction of Some PH-Acids with Dimethylformamide Diethyl Acetal.-PH-acids (I) smoothly react with dimethylformamide acetal (II) furnishing novel mono-or diphosphorus-containing compounds (III) or ( IV), resp., according to the proportion of reactants. -(PRISHCHENKO, A. A.; LIVANTSOV, M. V.; PETROSYAN, V. S.; Zh.

Chemistry of Phosphorylated Formaldehyde Derivatives. Part I

“…Compound 161 was obtained in 62% yield by heating a 2:1 mixture of diethyl phosphite ( 6 ) and dimethylformamide dimethylacetal ( 78 ) [27]. Dialkyl phosphites 51 , dialkyl- and diphenylphosphine oxides 52 , 53 can be also involved in this reaction [31,32,119]. Intermediate dialkyl [( N,N -dimethylamino)methoxymethyl]phosphonates ( 162 ) or dialkyl[( N,N -dimethylamino)-methoxymethyl]phosphine oxides 163 may be isolated in many cases [32,119].…”

“…Dialkyl phosphites 51 , dialkyl- and diphenylphosphine oxides 52 , 53 can be also involved in this reaction [31,32,119]. Intermediate dialkyl [( N,N -dimethylamino)methoxymethyl]phosphonates ( 162 ) or dialkyl[( N,N -dimethylamino)-methoxymethyl]phosphine oxides 163 may be isolated in many cases [32,119]. This allows preparation of symmetrical 164 and unsymmetrical diphosphinoyl N,N -dimethylaminomethanes 165 [31,32,119,120] (Scheme 47).…”

“…The general property of phosphorylated formaldehyde acetals 13 and structurally related compounds 14 – 16 is the possibility of phosphorus–carbon bond cleavage under the action of acids and acidic reagents [24,77,95,98], organic reagents [19,119], and bases [37,127,128].…”

“…The reaction of diethyl phosphite ( 6 ) with dipropyl [( N,N -dimethylamino)ethoxymethyl]phosphonate ( 191 ) is also accompanied by the partial cleavage of the phosphorus–carbon bond [119].…”