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Studies On The Reaction Of Arylallene With Diphenylphosphine Oxide And Application Of Sulfur-phosphorus Reagent SDDP

Posted on:2021-02-28Degree:MasterType:Thesis
Country:ChinaCandidate:X P YanFull Text:PDF
GTID:2381330605977073Subject:Chemistry
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The research content of this thesis is mainly divided into two parts namely;(1)studies on the reaction of aryl-substituted allenes with diphenylphosphine oxide and,(2)synthesis and application of the sulfur-phosphorus reagent SDDP.(1)Studies on the reaction of aryl-substituted allenes with diphenylphosphine oxideIn this part,a series of novel bisphosphonylation products of aryllidene were synthesized via the reaction of allenes and diphenylphosphine oxide.Furthermore,the mechanism of the reaction was studied and thus,a free radical pathway was proposed where three new chemical bonds are formed in one step via a concerted air-induced bisphosphonation-hydroxylation process.The structures of all the newly synthesized products were confirmed by 1H-,13C-,31P-NMR and high resolution mass spectrometry.Moreover,the structure of one of the representative products was confirmed by X-single crystal diffraction analysis.Notable benefits of this novel reaction include mild reaction conditions,good atom-and step-economy,as well as the rich chemistry of the synthesized products.(2)Synthesis and application of the sulfur-phosphorus reagent SDDPIn this part,the design,synthesis and reaction of the sulfur-phosphorus reagent SDDP were studied.Initially,the design and synthesis of the novel reagent SDDP was successfully carried out,and its structure was confirmed by spectroscopic methods.Thereafter,the synthetic application of the novel reagent SDDP was investigated via its reaction with aryl boronic acids,indole derivatives,acetophenone derivatives and thiols.Thus,the phosphorothiolation of aromatic rings,indoles,?-carbon of acetophenone derivatives and thiols were successfully carried out to afford dialkyl phosphorothioates derivitives of aromatics,indole derivatives,acetophenone derivatives,and thiols,respectively.Finally,the structures of all the newly synthesized compounds were confirmed by 1H-.13C-,31P-NMR and high resolution mass spectrometry.
Keywords/Search Tags:Aromatic allenes, diphenylphosphine oxide, phosphine acylation, sulfur phosphorus reagent
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