5836-28-2Relevant articles and documents
Tetrahydrofuran, one of the most popular solvents in organic synthesis, is not completely inert
Makowiec,Rachon
, p. 487 - 492 (2007/10/03)
Tetrahydrofuran undergoes fast ring cleavage in the reaction with PhI(OH)OTs/(RO)2P(O)H system, which causes the formation of O-(dialkoxyphosphoryl)-O′-tosyl-1,4-butanediol. This fact indicates that tetrahydrofuran is not suitable as a solvent for reactions with strong electrophilic reagents, such as hypervalent iodine reagents.
The reactions of dialkyl phosphites and phosphine oxides with iodosylbenzene
Makowiec, Slawomir,Rachon, Janusz
, p. 941 - 955 (2007/10/03)
The reaction of iodosylbenzene with > P(O)H type of acids (dialkyl phosphites, secondary phosphine oxides) was studied. The acids of >P(O)H type add to iodosylbenzene to yield intermediate 6 which in the aprotic solvents yields oxidation products, it means >P(O)OH acids and/or anhydride of >P(O)OP(O) P(O)OR ester is the major product.
ELECTROCHEMICALLY INDUCED PROCESSES OF FORMATION OF PHOSPHORIC ACID DERIVATIVES. 3. ELECTROSYNTHESIS FROM WHITE PHOSPHORUS IN ALCOHOL-WATER SOLUTIONS
Budnikova, Yu. G.,Kargin, Yu. M.,Zaripov, I. M.,Romakhin, A. S.,Ignat'ev, Yu. A.,et al.
, p. 1580 - 1584 (2007/10/02)
It has been established that the process of splitting of the P-P bonds of the white phosphorus molecules is initiated by cathode-generated nucleophiles (HO-, RO-), while functionalization of the P-H bond formed in phosphoric oligomers occurs under the action only of alcohol.The primary product after splitting of all the P-P bonds in phosphoric oligomers is dialkylphosphite (in alcohol-water media), or trialkylphosphite (in absolute alcohol), in the course of electrolysis being transformed into trialkylphosphate.Formation of esters of pyrophosphoric acid with reduced protogenic character of the medium was examined.It is proposed that under these conditions nucleophilic reagents of the type (>P)c-O- form and participate in splitting of the P-P bonds. Keywords: phosphoric acid derivatives, white phosphorus, electrosynthesis, alcohol-water solution.