- Direct, oxidative halogenation of diaryl- or dialkylphosphine oxides with (dihaloiodo)arenes
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The oxidative halogenation of diaryl- or dialkylphosphine oxides with the hypervalent iodine reagents (difluoroiodo)toluene (p-TolIF2, 1) and (dichloroiodo)benzene (PhICl2, 2) is reported. Phosphoric fluorides could be recovered in 32–75% yield, or they could be trapped with EtOH to give the corresponding phosphinate in typically good yield. Phosphoric chlorides were not readily isolable, and were trapped with alcohol and amine nucleophiles, giving diaryl- or dialkylphos-phinates and phosphinamides in up to 90% yield.
- Eljo, Jasmin,Murphy, Graham K.
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supporting information
p. 2965 - 2969
(2018/06/30)
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- Direct conversion of secondary phosphine oxides and h-phosphinates with [Di(acyloxy)iodo]benzenes to phosphinic and phosphonic amides
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The reaction of [di(acyloxy)iodo]- benzene with secondary phosphine oxides or H-phosphinates in the presence of primary or secondary amines allows one to obtain phosphinic or phosphonic acids amides in the one-pot process. We take advantage of the strong acylating system DAIB/R2P(O)H to phosphinylation of amines. However, the reaction mechanism is multipathway and causes yields of phosphinic or phosphonic acids amides to be moderate. When the concentration of amines is low, the intermolecular process plays a main role leading to the formation of carboxylic amides through mixed phosphoric-carboxylic anhydride, and also in the low concentration of amines, tetrahydrofuran effectively competes with the amines in the nucleophilic attack on the acylating intermediates.
- Hubacz, Anna,Makowiec, Slawomir
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experimental part
p. 81 - 86
(2009/09/25)
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- Reactivity of diacyloxyiodobenzenes toward trivalent phosphorus nucleophiles
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The reaction of diacyloxyiodobenzenes and tetravalent phosphorus nucleophiles was investigated. It was established that both H-phosphonates and secondary phosphine oxides react with diacetoxyiodobenzene in alcohols in the presence of sodium alcoholates yi
- Makowiec, Slawomir,Rachon, Janusz
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p. 352 - 359
(2007/10/03)
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- The reactions of dialkyl phosphites and phosphine oxides with iodosylbenzene
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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.
- Makowiec, Slawomir,Rachon, Janusz
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p. 941 - 955
(2007/10/03)
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