3302-83-8Relevant academic research and scientific papers
Cyclic phosphonium ionic liquids
Lall-Ramnarine, Sharon I.,Mukhlall, Joshua A.,Wishart, James F.,Engel, Robert R.,Romeo, Alicia R.,Gohdo, Masao,Ramati, Sharon,Berman, Marc,Suarez, Sophia N.
, p. 271 - 275 (2014)
Ionic liquids (ILs) incorporating cyclic phosphonium cations are a novel category of materials. We report here on the synthesis and characterization of four new cyclic phosphonium bis(trifluoromethylsulfonyl)amide ILs with aliphatic and aromatic pendant g
Reduction of tertiary phosphine oxides to phosphine-boranes using Ti(Oi-Pr)4/BH3-THF
Sowa, Sylwia,Pietrusiewicz, K. Micha?
supporting information, (2021/03/17)
A new method for reduction of tertiary phosphine oxides leading to the formation of tertiary phosphine-boranes has been developed. The BH3-THF/Ti(Oi-Pr)4 reducing system enables conversion of triaryl, diarylalkyl and trialkylphosphine oxides directly to their borane analogues in good to high yields. In contrast to the previously reported protocols, the presence of activating groups in the structure of starting material is not necessary for the reaction to occur. The reaction is highly stereoselective and proceeds with predominant retention of configuration at the phosphorus atom. A plausible mechanism of reduction of the P[dbnd]O bond by BH3-THF/Ti(Oi-Pr)4 has been proposed.
Raney-Ni reduction of phosphine sulfides
Demchuk, Oleg M.,?wierczyńska, Wioletta,Dziuba, Kamil,Frynas, S?awomir,Flis, Anna,Pietrusiewicz, K. Micha?
, p. 64 - 68 (2016/12/24)
A variety of tertiary phosphine sulfides have been reduced by Raney-Ni to give the corresponding phosphineswith high efficiency and undermild conditions. Alkyl, aryl, acyclic, cyclic, aswell as sterically crowded phosphine sulfides are reduced with equal facility. Optically active P-stereogenic phosphine sulfides are reduced stereospecifically with clean retention of configuration at P. Reductions of unsaturated phosphinesulfides is not fully chemoselective and takes place with concomitant partial reduction of the double bond. Clean reduction of the unsaturated phosphine sulfides to the corresponding fully saturated phosphines can be achieved in one step by running the reduction under H2atmosphere (balloon).
Organocatalyzed Reduction of Tertiary Phosphine Oxides
Schirmer, Marie-Luis,Jopp, Stefan,Holz, Jens,Spannenberg, Anke,Werner, Thomas
supporting information, p. 26 - 29 (2016/01/25)
A novel selective catalytic reduction method of tertiary phosphine oxides to the corresponding phosphines has been developed. Notably, the reaction proceeds smoothly with low catalyst loadings of 1-5 mol% even at low temperature (70 C). Under the optimized conditions various phosphine oxides could be selectively reduced and the desired phosphines were usually obtained in excellent yields above 90%. Furthermore, we have developed a one-pot reaction sequence for the preparation of valuable phosphinborane adducts. Simple addition of BH3THF subsequent to the reduction step gave the desired adducts in yields up to 99%.
In situ phosphine oxide reduction: A catalytic appel reaction
Van Kalkeren, Henri A.,Leenders, Stefan H. A. M.,Hommersom, C. Rianne A.,Rutjes, Floris P. J. T.,Van Delft, Floris L.
supporting information; experimental part, p. 11290 - 11295 (2011/10/19)
Several important reactions in organic chemistry thrive on stoichiometric formation of phosphine oxides from phosphines. To avoid the resulting burden of waste and purification, cyclic phosphine oxides were evaluated for new catalytic reactions based on in situ regeneration. First, the ease of silane-mediated reduction of a range of cyclic phosphine oxides was explored. In addition, the compatibility of silanes with electrophilic halogen donors was determined for application in a catalytic Appel reaction based on in situ reduction of dibenzophosphole oxide. Under optimized conditions, alcohols were effectively converted to bromides or chlorides, thereby showing the relevance of new catalyst development and paving the way for broader application of organophosphorus catalysis by in situ reduction protocols. Copyright
Trans stereoselectivity in the reaction of cyclic phosphonium salts with aromatic aldehydes
Lawrence, Nicholas J.,Beynek, Hayrettin
, p. 497 - 498 (2007/10/03)
The Wittig olefination of substituted aromatic aldehydes with ylides from phosphorinanium salts [RCH2P(Ph)(CH2)5]+Br- in which the phosphorus atom is incorporated into a six-membered ring, is E-selective.
Crystal Strucutres of Some Cyclic Phosphonium Salts and Their Relation to the Stereochemical Course
Gallucci, Judith C.,Holmes, Robert R.
, p. 4379 - 4386 (2007/10/02)
Single-crystal X-ray analyses of 1-benzyl-1-phenylphosphorinanium bromide (I) and 1,1-diphenyl-4-methylphosphorinanium bromide (II) showed that their structures are very similar.Each contains the six-membered ring in the chair form and in the case of I th
