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Dichlorophenylphosphine

About: Dichlorophenylphosphine is a(n) research topic. Over the lifetime, 127 publication(s) have been published within this topic receiving 1267 citation(s).


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Journal ArticleDOI
Abstract: The [1]ferrocenophanes, 1,1′-ferrocenediyldiphenylsilane, bis(1,1′-ferrocenediyl)silane, 1,1′-ferrocenediyldiphenylgermane and 1,1′-ferrocenediylphenylphosphine have been prepared by the reaction of 1,1′dilithioferrocenebis N , N , N′ , N′ -tetramethylethylenediamine) with dichlorodiphenylsilane, tetrachlorosilane, dichlorodiphenylgermane and P , P -dichlorophenylphosphine, respectively. Similar reactions with dichlorodimethyltin or dichlorodiphenyltin yielded only polymeric products. The Group IV [1]ferrocenophanes are red, air-stable, crystalline solids; the phosphorus compound is red-purple and is moderately air-sensitive. The spectroscopic properties of the compounds, which are consistent with ring-tilted structures, are reported and discussed.

147 citations

Journal ArticleDOI
TL;DR: Four novel phosphorus-selenium heterocycles, including a spirocyclic heterocycle exhibiting a four-membered P2SeC ring, were obtained from the reaction of WR with two reactive substrates (diphenylcyclopropenone and methyl phenylpropiolate).
Abstract: A new and improved method for the preparation of (PhPSe 2 ) 2 (Woollins reagent (WR), 1) is reported. Reaction of dichlorophenylphosphine with Na 2 Se, (prepared from the reaction of elemental selenium and sodium in liquid ammonia) gives WR with excellent purity, high yield and on a larger scale than was previously possible. Four novel phosphorus-selenium heterocycles, including a spirocyclic heterocycle exhibiting a four-membered P 2 SeC ring. were obtained from the reaction of WR with two reactive substrates (diphenylcyclopropenone and methyl phenylpropiolate). Useful selenocarbonyl and thiocarbonyl compounds were obtained from the reaction of both WR and Lawesson's reagent with diphenylcyclopropenone. All new compounds were characterised spectroscopically and three demonstrative X-ray structures are reported.

101 citations

Journal ArticleDOI
Abstract: Synthesis and reactions of new phosphine-boranes have been studied. Diastereomerically pure menthyloxyphenylphosphine-boranes were prepared from dichlorophenylphosphine. These secondary phosphine-boranes underwent stereospecific alkylation and arylation reactions. It is noted that the stereochemistry of palladium-catalyzed cross-coupling reactions was largely affected by the solvent and the base used. Thus, the reaction in acetonitrile proceeded with net retention of configuration. In sharp contrast, the reaction in THF in the presence of K2CO3 occurred with inversion of configuration with high degree of stereospecificity. The phosphorus-oxygen bond of the resulting phosphine-boranes was reductively cleaved at -78 "C by lithium naphthalenide or lithium in liquid ammonia in almost quantitative yields with an excellent degree of stereospecificity. On the other hand, the reactions at elevated temperatures provided the products with almost complete racemization. This racemization was proved to occur via pyramidal inversion of the anionic tricoordinate phosphorus species. Based on these results, we developed new methods for the synthesis of bidentate phosphine ligands with homochiral phosphine centers. Optically pure bisphosphinoethanes and bisphosphinobutanes possessing phenyl, t-butyl, cyclohexyl, emethomhenyl, methyl, or 2methoxyethyl group were prepared via phosphine-boranes. Functionalizations of the boranato group of phosphine-boranes have been investigated. Trimethylphosphine-borane reacted with methanesulfonic acid with evolution of hydrogen. The resulting trimethylphosphine-methylsulfonyloxyborane was subjected to nucleophilic substitution reaction on the boron atom with arenthiols or secondary phosphine-boranes. A new phosphine-borane having a P-B-P-B-P-B-P-B bond linkage was synthesized. Novel boron anion species were generated by the reaction of phosphine-monoiodoboranes with lithium 4,4'-dit -butylbiphenylide.

80 citations

Journal ArticleDOI
TL;DR: Treatment of dichlorophenylphosphine with two equivalents of carbonyl-decorated carbenes results in a two-electron reduction of the phosphorus centre concomitant with carbene oxidation to afford novel phosphaalkenes as confirmed via crystallographic, spectroscopic, and DFT analyses.
Abstract: Treatment of dichlorophenylphosphine with two equivalents of carbonyl-decorated carbenes results in a two-electron reduction of the phosphorus centre concomitant with carbene oxidation to afford novel phosphaalkenes as confirmed via crystallographic, spectroscopic, and DFT analyses.

77 citations

Journal ArticleDOI
TL;DR: This efficient Mo methylidyne synthesis permitted elaboration to an anionic phosphaisocyanide derivative upon deprotonation, functionalization with dichlorophenylphosphine, and ultimate reduction.
Abstract: Methine (CH) transfer to an open coordination site was achieved in one pot by titanium(III) abstraction of Cl from 7-chloronorbornadiene, radical capture by Mo, and benzene extrusion. This efficient Mo methylidyne synthesis permitted elaboration to an anionic phosphaisocyanide derivative upon deprotonation, functionalization with dichlorophenylphosphine, and ultimate reduction.

65 citations

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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20213
20201
20192
20184
20176
20164