- CsOH-promoted P-alkylation: A convenient and highly efficient synthesis of tertiary phosphines
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A mild and efficient method for the synthesis of tertiary phosphines and ditertiary phosphines has been developed. In the presence of cesium hydroxide, molecular sieves and DMF at room temperature, various secondary phosphines and alkyl bromides were examined, and the results have demonstrated that this methodology offers a general synthetic procedure to produce tertiary phosphines in moderate to high yields. Optically active tertiary phosphine synthesis is also described.
- Honaker, Matthew T.,Sandefur, Benjamin J.,Hargett, James L.,McDaniel, Alicia L.,Salvatore, Ralph Nicholas
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p. 8373 - 7377
(2007/10/03)
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- A new, stereoselective interconversion of phosphinothio-phosphinoseleno compounds, reduction of phosphinoseleno derivatives and retro pishchimuka rearrangement based on methylthio- and methylselenophosphonium salts chemistry
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The interconversion of thiono- into seleno compounds was found to proceed with retention of the configuration at phosphorus and the mechanistic course of this process has been proposed. The isomerization reaction of phosphinothiolates into thiono-isomers via the phosphonium salts has been developed and considered as the "retro Pishchimuka" rearrangement.
- Omelanczuk, Jan
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p. 8887 - 8898
(2007/10/02)
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- Preparation of Alkylmethylphenylphosphines by the Method of Hewertson and Watson
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The reaction of C6H5(CH3)PNa with some alkyl halides in liquid ammonia was studied.The resulting phosphines were characterized by elemental analyses, NMR spectra, and by the reaction with trimethylsilyl azide giving trimethylsilylimino triorganophosphoranes. - Keywords: Alkylmethylphenylphosphines, N-Trimethylsilylimino Triorganophosphoranes, NMR Spectra
- Wolfsberger, Werner
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p. 295 - 298
(2007/10/02)
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- SILYLPEROXIDES AS SELECTIVE OXYGENATION REAGENTS IN PHOSPHORUS CHEMISRTY
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Bis(trimethylsilyl)peroxide (BSPO) can be used for chemo- and stereoselective generation of P=O group by oxygenation of P(III) centre and transformation of P=S and P=Se groups.
- Kowalski, Jozef,Wozniak, Lucyna,Chojnowski, Julian
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p. 125 - 128
(2007/10/02)
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- A GENERAL SYNTHESIS OF OPTICALLY ACTIVE PHOSPHINES, PHOSPHINITES AND THIOPHOSPHINITES FROM ALKYLTHIO(ALKYLSELENO)PHOSPHONIUM SALTS AND TRIS(DIMETHYLAMINO)PHOSPHINE AS A THIOPHILIC AGENT
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Tris(dimethylamino)phosphine was found to be a suitable thiophilic reagent which converts optically active alkylthio(alkylseleno)phosphonium salts into chiral tertiary phosphines and phosphonites with a high stereoselectivity.The first synthesis of optically active thiophosphinites from bis(alkylthio)phosphonium salts and tris(dimethylamino)phosphine is also reported.
- Omelanczuk, J.,Mikolajczyk, M.
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p. 2493 - 2496
(2007/10/02)
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- PHOSPHORORGANISCHE VERBINDUNGEN 104. TERTIAERE PHOSPHINE BZW. ARSINE DURCH REDUKTIVE SPALTUNG QUARTAERER PHOSPHONIUM- UND ARSONIUMSALZE MIT ALKALIAMALGAMEN
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The reductive cleavage of achiral and optical active quaternary phosphonium and arsonium salts with alkali metal amalgams forming tertiary phosphines and tertiary arsines succeeds in high yields at room-temperature with retention of configuration.In the r
- Horner, Leopold,Dickerhof, Karlheinz
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p. 213 - 218
(2007/10/02)
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- Mechanisms in Electrophilic Reactions of Reactive Nitrogen Compounds with Phosphanes
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Chiral phosphanes were used as nucleophiles in reactions with reactive nitrogen compounds to investigate the mechanisms by stereochemical means:a) Retention on phosphorus occurs in the amination with O-(mesitylsulfonyl)hydroxylamine consistent with a Ssu
- Heesing, Albert,Steinkamp, Heinz
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p. 2854 - 2864
(2007/10/02)
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- Stereospecific Synthesis of Diastereoisomerically Pure (-)-(RP)-O-Mentyl Methylphenylphosphinite and Ethylphenylphosphinite: Key Intermediates in Synthesis of Chiral Tertiary Phosphines
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The reaction of the diastereoisomerically pure (-)-(RP)-O-mentyl methylphenylphosphinite (9) and (-)-(RP)-O-mentyl ethylphenylphosphinite (2) with organolithium reagents has been found to give chiral tertiary phosphines (10) and (11) with a very high optical purity.
- Omelanczuk, Jan,Perlikowska, Wieslawa,Mikolajczyk, Marian
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- Preparation and (31)P nuclear magnetic resonance studies of chiral phosphines
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The reaction of Li metal with alkyldiphenylphosphines generates the alkylphenylphosphide anions, which can undergo subsequent reactions with alkyl halides to give chiral phosphines (RR'R''P).The (31)P nmr chemical shifts have been measured for these phosphines, and show greater deviations from the values predicted by the first order additivity model than do those of more symmetrical phosphines (i.e., R3P and R2R'P).The shifts for these chiral molecules, and for a wide range of other phosphines, can be accurately predicted using a second order pairwise additivity scheme.The dependence of the observed and calculated chemical shifts upon electronegativity and steric factors is discussed.
- Payne, Nicholas C.,Stephan, Douglas W.
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- Phosphinegold (I) salts having antiarthritic activity
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The compounds are (pyridine) (trisubstituted phosphine) gold(I) salts which have antiarthritic activity.
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- Tri-substituted phosphinegold(I) 1-thio-β-D-glucopyranosides
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The compounds are tri-substituted phosphinegold(I) 1-thio-β-D-glucopyranosides which have antiarthritic activity and, in particular, are of use in the treatment of rheumatoid arthritis. Of the three substituents on the phosphine one is optionally substituted phenyl and the others are lower alkyl or lower alkoxy.
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