Topic
Dichlorophenylphosphine
About: Dichlorophenylphosphine is a research topic. Over the lifetime, 127 publications have been published within this topic receiving 1267 citations.
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TL;DR: In this article, the first 2-Phenyl-1,2-oxaphospholane (1a), 2-phenyl- 1,2oxaphophosphorinane (2b), 2phenyl 1, 2-thiaphosphorine (2c), and 2-phenyl 1 2,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,
Abstract: 2-Phenyl-1,2-oxaphospholane (1a), 2-phenyl-1,2-oxaphosphorinane (1b), 2-phenyl-1,2-thiaphospholane (1c), and 2-phenyl-1,2-thiaphosphorinane (1d) were prepared readily by the reaction of dichlorophenylphosphine with an ω-chloroalkanol or an ω-chloroalkanethiol followed by cyclization with the aid of lithium metal. Compounds 1b–d have been obtained for the first time.
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TL;DR: In this article, 6-phenyl-6H-benzo[f]naphtho[2,3-b]phosphoindole was prepared by reacting dichlorophenylphosphine with a dilithium intermediate derived from 3,3′-dibromo-2,2′-binaphthyl.
Abstract: Phosphole-fused π-conjugated acenes have been attracting interest because of the attractive features of the phosphole moiety, such as fluorescence and chemically modifiable properties. Herein, 6-phenyl-6H-benzo[f]naphtho[2,3-b]phosphoindole was prepared by reacting dichlorophenylphosphine with a dilithium intermediate derived from 3,3′-dibromo-2,2′-binaphthyl. Various derivatives, such as a phospholium salt and a borane–phosphole complex with functional groups on the phosphorus atom were synthesized using the obtained phosphole as a common starting material. Single-crystal X-ray analysis of the parent benzo[f]naphtho[2,3-b]phosphoindole revealed that the pentacyclic ring is almost planar. Fluorescence spectroscopy data showed that the phosphole derivatives, such as phosphine oxide and the phospholium salt and borane complex exhibited photoluminescence in chloroform.
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TL;DR: In this paper, the synthesis and reactions of new phosphine-boranes have been studied and new methods for the synthesis of bidentate phosphine ligands with homochiral phosphine centers were developed.
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.
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TL;DR: The formation of alkyl chlorides in the reactions of alcohols with phosphorus trichloride, dichlorophenylphosphine, or chlorodiphenyl phosphine involves the dealkylation of an intermediate phosphorus(III) ester by hydrogen chloride as mentioned in this paper.
Abstract: The formation of alkyl chlorides in the reactions of alcohols with phosphorus trichloride, dichlorophenylphosphine, or chlorodiphenylphosphine involves the dealkylation of an intermediate phosphorus(III) ester by hydrogen chloride (Scheme 1).1–3 An analogous dealkylation occurs in the reactions of hydrogen chloride with triphenyl phosphite-alcohol mixtures (Scheme 2).4
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TL;DR: Based on the coupling of an arylzinc reagent, an internal alkyne, and dichlorophenylphosphine, a new synthesis of benz[b]phosphole derivatives is presented in this article.
Abstract: Based on the coupling of an arylzinc reagent, an internal alkyne, and dichlorophenylphosphine a new synthesis of benz[b]phosphole derivatives is presented.