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Investigations On The Several Cyclization Reactions Of [60]Fullerene

Posted on:2010-11-03Degree:DoctorType:Dissertation
Country:ChinaCandidate:B ZhuFull Text:PDF
GTID:1101360275455570Subject:Organic Chemistry
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Chemical modification is one of the most important research fields in the fullerene chemistry.Many fuUerene derivatives have been synthesized hitherto,and have potential applications in material and medicine science.Among these various functionalization methods,cycloaddition reactions are among the pioneering and most studied reactions in fullerene chemistry.In this dissertation,we synthesized several new types of fullerene derivatives through four new cyclization reactions.1.It was found that the reactions of C60 with anthranilic acids and isoamyl nitrite in the presence of triethylamine unexpectedly afforded C60-fusedδ-lactones,which would be difficult to be prepared by other known methods.The effect of various bases used on the reaction and the reaction scope were investigated.2.The reactions of C60 with unsaturated aldehydes and anhydrides in the presence of p-toluenesulfonic acid afforded a series of C60-fused cyclohexene derivatives,one of which underwent further functionalization gaving an open-cage fullerene product.3.The palladium-catalyzed heteroannulations of C60 with a variety ofο-iodoanilines afforded the first synthesis of C60-fused indoline derivatives.The effect of various ligands and bases used on the reaction and the reaction scope were investigated.A plausible reaction mechanism for the formation of products was also proposed.4.Utilizing C-H bond activation strategy,the annulations of C60 with various anilides promoted by the combination of Pd(OAc)2 and PTSA were realized, affording[60]fulleroindolines in good yield and high regioselectivity.The reaction scope was investigated and a plausible reaction mechanism was proposed.
Keywords/Search Tags:fullerene, C60, annulation, triethylamine, anthranilic acid, δ-lactone, cyclohexene, open-cage fullerene, o-iodoaniline, indoline, C-H bond activation, anilide
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