Study On Green Chemistry Reaction Of Aromatic Nitro Compounds With β-Cyclodextrin/NaOH System

In the thesis, we investigated chemical reactivity of aromatic nitro compounds in the presence of β-cyclodextrin (β-CD) in sodium hydroxide solution and the tentative reaction mechanism. β-CD is cyclic oligosaccharides consisting of 7 glucose units connected by α-1,4-glycoside bonds. The CD molecule has the shape of a truncated cone. The exterior of cyclodextrin is hydrophilic, however, the interior of cyclodextrin is hydrophobic. β-CD with hydrophobic cavity could form inclusion complexes with a variety of guest molecules. The complexation depends on the size, shape and hydrophobicity of the guest molecule. β-CD is widely used in organic synthesis because hydrophobic cavity can exert microenvironmental effects leading to selective reactions.Aromatic nitro compounds have been found to exhibit special reaction behavior in the presence of β- CD in sodium hydroxide solution by our research group for the first time. In the thesis, we investigated chemical reactivity of some familiar aromatic nitro compounds with β-CD/NaOH system and put forward the tentative reaction mechanism. Various substituted aromatic nitro compounds were converted into different products in the reaction conditions due to different property and position of substituents. Acquired research results as follows:(1) Most of aromatic nitro compounds were selectively reduced to the corresponding azoxy compounds with β-CD/NaOH system, which can offer a new synthetic methodology of aromatic azoxy compounds.(2) Hydrolysis of p-nitroanisole and p-nitrophenetole gave p-nitrophenol in the presence of β-CD in alkaline aqueous solution.(3) p-Nitrotoluene and p-ethylnitrobenzene produced carbon-carbon coupling products with β-CD/NaOH system, which can provide a new method of the formation of carbon-carbon bond and increase of carbon chain.(4) Aromatic dinitro compounds were reduced irrespective of the presence or absence of β-CD in sodium hydroxide solution, which revealed particularity of aromatic dinitro compounds.These reactions have advantages below over past research results of aromatic nitro compounds:(1) The synthetic method using water as the reaction medium may...