Study On The Conversion Reaction Of Nitrosoarene Induced By Visible Light

Nitroso compounds(R-N=O)are an important class of synthetic substrates in synthetic organic chemistry and have been used in a wide range of synthetic reactions such as cycloaddition reactions,Hetero-Diels-Alder reactions,Aldol reactions and nitroso-alkene reactions.In addition,nitroso compounds have shown unique reactivity and application in the construction of complex natural product molecules.Literature research has revealed that the reported transformations of nitroso compounds are mainly focused on transition metal catalysis as well as thermal catalysis.In recent years,the use of green and clean visible light to induce transformations in organic synthesis has been developed considerably.However,the photochemical conversion of nitroso compounds under visible light-induced conditions has rarely been reported.Therefore,the development of ne w chemical transformations of nitroso compounds induced by visible light has certain research value and theoretical guidance.In the first chapter of this thesis,the reactions involving nitroso compounds are reviewed through six aspects: cycloaddition reactions,Hetero-Diels-Alder reactions,Aldol reactions,nitroso-alkene reactions,and nitroso compounds as radical acceptors and carbine-capture reagents.In the second chapter of this thesis,the visible light-induced [3+2]-cycloaddition reaction of a nitroso-arene and 2H-azirines was achieved using a nitroso-arene as a radical acceptor.This reaction provides a new green and efficient route for the photochemical synthesis of 1,2,4-oxadiazoles as heterocyclic compounds.In Chapter 3 of this thesis,the photochemical synthesis of nitrone analogues was achieved using nitrosoaromatics as carbine-capture reagents.The reaction occurs under a single visible light irradiation,is efficiently synthesised without any catalysts or additives,and shows good functional group tolerance to both aryl diazoesters and nitrosoaromatics.