摘 要

论文以环戊二烯为原料，经过环氧化和叠氮化等多步反应合成四氢环戊二烯醇衍生物。讨论了投料比、温度、pH值、溶剂和缚酸剂对产率的影响。确定了环氧化第一步的最佳优化条件，反应温度在0-4℃之间，反应时间为2小时，溶剂为二氯甲烷，缚酸剂为碳酸钾。确定了环氧化第二步的最佳优化条件，反应温度在0-4℃之间，反应时间为24小时，溶剂为氯仿，缚酸剂为碳酸钾，投料比为1:1.1。分别用GC和¹H-NMR对产物进行了鉴定。

关键词：环氧化反应; 过氧乙酸; 间氯过氧苯甲酸; 叠氮化钠；

ABSTRACT

The derivatives of tetrahydrocyclopentadienol was synthesized via two epoxidations of cyclopentadiene, followed by reaction with sodium azide. The reactant ratio, acid-binding agent, pH value and reaction temperature was discussed to improve the yield. The optimum conditions were determined. For the first step, the reaction temperature was within the range of 0-4℃, the reaction time was 2 hours, the solvent was methylene chloride and the acid-binding agent was potassium carbonate. For the second step, the reaction temperature was varied from 0-4℃, the reaction time was 24 hours, the solvent was chloroform, the acid-binding agent was potassium carbonate and the reactant ratio of the substrate and m-chloroperoxybenzoic acid was 1: 1.1. The products structure were proved by GC and ¹H-NMR respectively.

Key Words: epoxidation reaction; peracetic acid; m-chloroperoxybenzoic acid; sodium azide;

目录

摘要……………………………………………………………………………………I

ABSTRACT………………………………………………………………………..Ⅱ

目录………………………………………………………………………………….Ⅲ

1. 文献综述………………………………………………………………….1
   1. 前言………………………………………………………………………………1
   2. 环戊二烯的环氧化………………………………………………………………3

1.2.1 6-氧杂-双环[3.1.0]己-2-烯的合成………………………………………4

• • 1. 3,7-二氧杂-三环[4.1.0.0^2,4]庚烷的合成………………………………...4

1.2.3 其它环氧化合成路线…………………………………………………..…5

• 1. 叠氮加成制备四氢环戊二烯醇衍生物…………………………………………7
  2. 选题的研究问题和解决途径…………………………………………………....8

第二章 6-氧杂-双环[3.1.0]己-2-烯的合成……………………………..........9

2.1 反应原理………………………………………………………………………….9

2.2 试剂与仪器……………………………………………………………………….9

2.2.1 试剂………………………………………………………………………..9

2.2.2 仪器………………………………………………………………………..9

2.3 实验部分………………………………………………………………………...10

2.3.1二聚环戊二烯的裂解…………………………………………………….10

2.3.2过氧乙酸的合成………………………………………………………….10

2.3.3 6-氧杂-双环[3.1.0]己-2-烯的制备……………………………………….10

2.3.4 提纯与精制………………………………………………………………11

2.4 结构鉴定………………………………………………………………………...11

第三章 3,7-二氧杂-三环[4.1.0.0^2,4]庚烷的合成……………….………….13

3.1 反应原理………………………………………………………………………...13

3.2 试剂与仪器……………………………………………………………………...13

3.2.1 试剂………………………………………………………………………13

3.2.2 仪器………………………………………………………………………14

3.3 实验部分………………………………………………………………………...14

3.3.1 3,7-二氧杂-三环[4.1.0.0^2,4]庚烷的合成……………………………….14

3.3.2 溶剂的选择………………………………………………………………14

3.3.3 投料比的优化……………………………………………………………15

3.3.4 缚酸剂的选择……………………………………………………………15

3.3.5 pH值的优化……………………………………………………………15

3.3.6 提纯与精制………………………………………………………………15

3.3.7 结果与讨论………………………………………………………………16

3.4 结构鉴定………………………………………………………………………...17

第四章 四氢环戊二烯醇衍生物的制备…………………………………….19

4.1 反应原理………………………………………………………………………...19

4.2 试剂与仪器……………………………………………………………………...19

4.2.1 试剂………………………………………………………………………19

4.2.2 仪器………………………………………………………………………19

4.3 实验部分………………………………………………………………………...20

4.3.1 使用叠氮化钠的注意事项………………………………………………20

4.3.2 实验步骤…………………………………………………………………20

4.3.3 实验条件的优化…………………………………………………………20

第五章 结论与展望……………………………………………………………..22

5.1 结论……………………………………………………………………………...22

5.2 展望……………………………………………………………………………...22

参考文献…………………………………………………………………………...23

致谢………………………………………………………………………………….26

第一章 文献综述

1.1前言

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