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Electrochemical Oxidation Synthesis Of1,3,4-oxadiazoles And α,α-dichloro Ketones

Posted on:2015-03-01Degree:MasterType:Thesis
Country:ChinaCandidate:H Y MaFull Text:PDF
GTID:2251330428999729Subject:Organic Chemistry
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Organic electrochemical synthesis, referred to as organic electrochemistry, is combined electrochemical with organic chemistry, an interdisciplinary combination. With the applications of electron in organic compounds, while electron is the most commonly used in the electrochemical process, it can make the organic compounds being oxidized or reduced to achieve the ideal compounds. The basic types of electrochemical methods including the carbon-carbon bond formation and addition of functional groups, substitution, cleavage, elimination, coupling, oxidation, reduction and the use of electronic media indirect synthesis reactions.With the development of science and technology, and the worsening global environment, chemists have been able to make the effort to realize chemical reactions which can be more moderate reaction conditions, more simple reaction process and more friendly to environmentally. Organic scientists are constantly trying to reduce the environmental pollution caused by the reaction process by use different means of experiments. Due to electrochemical synthesis are using electron as an oxidation/reduction agent and the reaction conditions are relatively mild, very friendly to the environment etc., it is more conform to the current requirements of green chemistry.This thesis describes the electrochemical oxidation of1,3,4-oxadiazoles, α,α-dichloro ketones. It mainly consists of two parts, the first part focuses on the famous organic chemists’achievements about1,3,4-oxadiazoles, a,a-dichloro ketones; second part details the organic electrochemical synthesis1,3,4-oxadiazoles, a,a-dichloro ketones methods.At first, we achieved using the aryl hydrazide directly formed to2,5-disubstituted1,3,4-oxadiazole. The current method of synthesis such compounds generally requires the use of a toxic metal catalyst or a complex non-metal complex catalyst system. Although these methods can get a better reaction yield, but the reaction itself, often because of the use of expensive catalysts or reaction conditions is stringent or more complex post-processing and other reasons, limit their further application in organic synthesis. However, we successfully achieved by electrochemical organic synthesis methods, in mild reaction conditions, simple post-processing to generate1,3,4oxadiazoles, the reaction has many advantages such as efficient, green environmentally friendly.Furthermore, we used dilute hydrochloric acid (HCl) as a chlorine source, the realization of the aromatic acetylene compound to α,α-dichloro ketones. Synthesis of such compounds in present method, the reaction often uses an excess of an inorganic acid or an organic acid having toxicity, limiting the development of the reaction. We generated by electrochemical organic synthesis a,a-dichloro ketones, the reaction yield is good in mild reaction conditions, so the reaction has important industrial applications.We succeed in combing organic synthesis and electrochemical means, to synthesize1,3,4-oxadiazole, a,a-dichloro ketone compound in a more green chemistry way. The reaction is using a large amount of electrons as the oxidant and the reaction system is suitable for different substrates. The reaction which has mild reaction conditions and good yield is not only has a very important application value, but also makes the organic synthesis greener in new direction.
Keywords/Search Tags:Organic electrosynthesis, Green chemistry, 1,3,4-oxadiazole, α,α-dichloro ketone
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