repository
Up-Scale Synthesis of p-(CH2=CH)C6H4CH2CH2CH2Cl by CuCN Catalyzed Coupling Reaction of Grignard Reagent with BrCH2CH2CH2Cl
- Author(s)
- 박주용
- Advisor
- 이분열
- Department
- 일반대학원 분자과학기술학과
- Publisher
- The Graduate School, Ajou University
- Publication Year
- 2023-02
- Language
- kor
- Keyword
- CuCN catalyst; Grignard reagents; PhCu(CN)Mg(THF)4Cl crystal; coupling reaction; large scale
- Alternative Abstract
- Grignard reagents featuring carbanion characteristics are generally unreactive toward alkyl halides and require a catalyst for the coupling reaction. With the need to synthesize p-(CH2=CH)C6H4CH2CH2CH2Cl on a large-scale, the coupling reaction of p-(CH2=CH)C6H4MgCl with BrCH2CH2CH2Cl was attempted to screen the catalysts, and CuCN was finally determined to be the best catalyst affording the desired compound in 80% yield with no generation of Wurtz coupling side product CH2=CHC6H4C6H4CH=CH2. The p-(CH2=CH)C6H4Cu(CN)MgCl species was proposed as an intermediate based on the X-ray structure of PhCu(CN)Mg(THF)4Cl. The structures of p-(CH2=CH)C6H4CH2CH2CH2MgCl and p-ClC6H4MgCl were also elucidated, which existed as an aggregate with MgCl2, proposing that some portion of the Grignard reagents were possibly lost in the coupling reaction owing to co-precipitation with the byproduct MgCl2. Using the developed syntheses, [p-(CH2=CH)C6H4CH2CH2CH2]2Zn which is latently useful compound for the production of PS-block-PO-block-PS, respectively, was successfully synthesized with considerable cost reductions.
- Fulltext
- Appears in Collections:
- Graduate School of Ajou University > Department of Molecular Science and Technology > 3. Theses(Master)
- Files in This Item:
- There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.
-
- License
- STATISTICS
- Total Visit :5,239,790
- Total Download :2,137
- Today View :7,624
