【作者】 余浩杰；

【导师】 赵华绒；

【作者基本信息】 浙江大学 ， 有机化学， 2006， 硕士

【摘要】 本论文由以下两大部分组成: 第一部分:文献综述部分。 分类概述了硒代羧酸酯的合成研究概况,以及作为一类非常有用的有机合成中间体在有机合成中应用的研究进展。对于硒代羧酸酯作为酰基自由基前体,所参与的多种分子内及分子间的反应及其机理进行了较全面的介绍和评述。 第二部分:正文部分。 研究了由硒代酰胺出发合成二酰基二硒醚和二茂铁硒代羧酸酯的简便合成方法,并且对反应机理进行了讨论。 1.介绍了硒代酰胺合成研究的进展,并合成了芳基硒代酰胺作为下一步反应的原料。 2.对硒代酰胺与酰氯在氯仿溶液中发生的硒转移反应进行了研究,并合成得到了一系列二酰基二硒醚,对该反应机理进行了探讨。该合成路线具有反应条件温和,原料易得,反应时间短,操作简便,产率高等特点。该路线提供了一种合成二酰基二硒醚新的简便合成方法。 3.介绍了二茂铁及其衍生物的合成方法及其广泛的应用情况。在相转移催化下以二茂铁酰氯、硒代酰胺和卤代烃为原料,用一锅法以及两步法两种合成路线,分别合成得到了一系列二茂铁硒代羧酸酯,并对各种卤代烃的反应情况进行了讨论。首次报道在两相催化反应体系中合成二茂铁硒代酯,得到一系列的新的二茂铁硒代羧酸酯化合物,同时为二茂铁硒代羧酸酯的合成提供了一条新的有效的路线。更多还原

【Abstract】 This dissertation consists of two parts.In the first part, we summarize the synthesis of selenol esters and the advance in the applications of Selenol esters as important reagents and intermediates in organic synthesis. Selenol esters have been employed as precursors of acyl radicals for several kinds of intermolecular and intramolecular free radical reactions. The mechanism of these typical free radical reactions are introduced and discussed.In the second part, we report a convenient synthesis of diacyl diselenides and develop the new routes for the preparation of ferrocenoyl selenol esters. The mechanisms of these reactions are proposed and discussed.In the first chapter, we prepare the arylselenoamides which is the starting material for the subsequent reactions.In the second chapter, we synthesize a series of diacyl diselenides by the reaction of arylselenoamides with acyl chlorides using chloroform as solvent. The mechanism of this reaction is proposed and discussed. We provide a new convenient method for the synthesis of diacyl diselenides.In the last chapter, we introduce the synthesis and extensive applications of ferrocene and ferrocene derivatives. A series of ferrocenoyl selenol esters were synthesized, using arylselenoamides with ferrocenoyl halides and organic halides, under liquid-liquid phase-transfer conditions. We find two routes for the preparation: the one pot synthesis and the two-step synthesis. We also discuss the mechanism of these reactions when using different kinds of organic halides.This is the first report of the synthesis of ferrocenoyl selenol esters under liquid-liquid phase-transfer conditions. We synthesize a series of new compounds, and provide new efficient methods for the synthesis of ferrocenoyl selenol esters.更多还原