| Nucleophilic Substitution on Porphyrin Ring： Synthesis of 2-（2-Hydroxynaphthyl）-5,10,15,20-tetraphenylporphyrin |
| |
| 引用本文： | 陈彰评,胡琴,翟保评,姜中兴,秦玮.Nucleophilic Substitution on Porphyrin Ring： Synthesis of 2-（2-Hydroxynaphthyl）-5,10,15,20-tetraphenylporphyrin[J].中国化学,2007,25(2):250-253. |
| |
| 作者姓名： | 陈彰评 胡琴 翟保评 姜中兴 秦玮 |
| |
| 作者单位： | College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, China |
| |
| 基金项目： | Project supported by the National Natural Science Foundation of China （No. 29872033）. |
| |
| 摘 要： | The reactions of 2-nitro-5,10,15,20-tetraphenylporphyrin （1） and its Ni （Ⅱ） （2）, Cu （Ⅱ） （3）, Zn （Ⅱ） （4） complexes with sodium 2-naphthoxide have been investigated in different solvents for preparing 2-substituted porphyrins. 2-（2-Hydroxynaphthyl）-5,10,15,20-tetraphenyl porphyrin （5） and its Ni （Ⅱ） （6）, Cu （Ⅱ） （7）, Zn （Ⅱ） （8） complexes were obtained in 72%, 78%, 81% and 65% yields in 2-naphthol at 150 ℃ respectively. The same products were also obtained in other protic solvents such as diglycol and diglycol monomethyl ether. When the reactions proceeded in aprotic solvent DMF at 150 ℃, besides 5 （70%）, 6 （34%）, 7 （54%） and 8 （50%）, the corresponding 2-（2-naphythoxy）-5, 10,15,20-tetraphenylporphyrin （9）, and its Ni （Ⅱ） （10）, Cu （Ⅱ） （11）, Zn （Ⅱ） （12） complexes were also obtained in minor, 40%, 18% and 2% yields respectively, but only 5, 6, 7, 8 were found at room temperature in DMF or DMSO. These reactions axe much faster than those of 1-4 with sodium phenoxide. The formation of C-coupling products 5-8 was proposed via SRN 1 mechanism.
|
| 关 键 词： | 二甘醇 耦合反应 光合成 大环化合物 |
| 修稿时间： | 2006-04-252006-10-25 |
Nucleophilic Substitution on Porphyrin Ring: Synthesis of 2‐(2‐Hydroxynaphthyl)‐5,10,15,20‐tetraphenylporphyrin |
| |
| CHEN, Zhang-Ping HU, Qin ZHAI, Bao-Ping JIANG, Zhong-Xing Qin, Wei.Nucleophilic Substitution on Porphyrin Ring: Synthesis of 2‐(2‐Hydroxynaphthyl)‐5,10,15,20‐tetraphenylporphyrin[J].Chinese Journal of Chemistry,2007,25(2):250-253. |
| |
| Authors: | CHEN Zhang-Ping HU Qin ZHAI Bao-Ping JIANG Zhong-Xing Qin Wei |
| |
| Institution: | College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, China |
| |
| Abstract: | The reactions of 2‐nitro‐5,10,15,20‐tetraphenylporphyrin ( 1 ) and its Ni (II) ( 2 ), Cu (II) ( 3 ), Zn (II) ( 4 ) complexes with sodium 2‐naphthoxide have been investigated in different solvents for preparing 2‐substituted porphyrins. 2‐(2‐Hydroxynaphthyl)‐5,10,15,20‐tetraphenyl porphyrin ( 5 ) and its Ni (II) ( 6 ), Cu (II) ( 7 ), Zn (II) ( 8 ) complexes were obtained in 72%, 78%, 81% and 65% yields in 2‐naphthol at 150 °C respectively. The same products were also obtained in other protic solvents such as diglycol and diglycol monomethyl ether. When the reactions proceeded in aprotic solvent DMF at 150 °C, besides 5 (70%), 6 (34%), 7 (54%) and 8 (50%), the corresponding 2‐(2‐naphythoxy)‐5, 10,15,20‐tetraphenylporphyrin ( 9 ), and its Ni (II) ( 10 ), Cu (II) ( 11 ), Zn (II) ( 12 ) complexes were also obtained in minor, 40%, 18% and 2% yields respectively, but only 5 , 6 , 7 , 8 were found at room temperature in DMF or DMSO. These reactions are much faster than those of 1 – 4 with sodium phenoxide. The formation of C‐coupling products 5 – 8 was proposed via SRN1 mechanism. |
| |
| Keywords: | 2‐nitro‐5 10 15 20‐tetraphenylporphyrin nucleophilic substitution 2‐(2‐hydroxynaphthyl)‐5 10 15 20‐tetraphenyl‐porphyrin 2‐naphthoxide anion |
| 本文献已被 维普 等数据库收录！ |
|
