Highly efficient synthesis of stereodefined multisubstituted 1,4-dicyano- and 1-cyano-1,3-butadienes and their reactions with organolithium reagents
文献类型：期刊论文
| 作者 | Wang, Congyang; Wang, Chao; Wang, Qifeng; Wang, Zhihui; Sun, Hui; Guo, Xiangyu; Xi, Zhenfeng |
| 刊名 | CHEMISTRY-A EUROPEAN JOURNAL
 |
| 出版日期 | 2007 |
| 卷号 | 13期号:22页码:6484-6494 |
| 关键词 | Butadienes Lithiation Nitriles Stereoselectivity Synthetic Methods |
| ISSN号 | 0947-6539 |
| DOI | 10.1002/chem.200700028 |
| 英文摘要 | Stereodefined multisubstituted 1-cyano- and 1,4-dicyano-1,3-butadiene derivatives were obtained in excellent yields of the isolated product from their corresponding monohalo and dihalobutadienes and CuCN. This reaction proceeded with high stereoselectivity and retention of the stercochemistry of the starting halobutadienes. A study of the utility of the thus-obtained 1-cyano- and 1,4-dicyano-1,3-butadiene derivatives was demonstrated by their reactions with organolithium reagents. 2H-Pyrrole or iminocyclopentadiene derivatives were formed in high yields from 1-cyano-4halo-1,3-butadienes and organolithium reagents. When 1,4-dicyano-1,3-butadienes were treated with organolithium reagents followed by trapping with electrophiles, a tandem process took place to afford 2H-pyrrolyl nitriles in excellent yields. Reduction of 1,4-dicyano-1,3-butadiene derivatives with LiAlH4 showed novel reaction patterns relative to normal nitriles. |
| 语种 | 英语 |
| WOS记录号 | WOS:000248558800022 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/62657]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Xi, Zhenfeng |
| 作者单位 | 1.Peking Univ, Coll Chem, Minist Educ, Key Lab Bioorgan Chem & Mol Engn,BNLMS, Beijing 100871, Peoples R China 2.Chinese Acad Sci, Inst Chem, Beijing 100080, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China |
| 推荐引用方式 GB/T 7714 | Wang, Congyang,Wang, Chao,Wang, Qifeng,et al. Highly efficient synthesis of stereodefined multisubstituted 1,4-dicyano- and 1-cyano-1,3-butadienes and their reactions with organolithium reagents[J]. CHEMISTRY-A EUROPEAN JOURNAL,2007,13(22):6484-6494. |
| APA | Wang, Congyang.,Wang, Chao.,Wang, Qifeng.,Wang, Zhihui.,Sun, Hui.,...&Xi, Zhenfeng.(2007).Highly efficient synthesis of stereodefined multisubstituted 1,4-dicyano- and 1-cyano-1,3-butadienes and their reactions with organolithium reagents.CHEMISTRY-A EUROPEAN JOURNAL,13(22),6484-6494. |
| MLA | Wang, Congyang,et al."Highly efficient synthesis of stereodefined multisubstituted 1,4-dicyano- and 1-cyano-1,3-butadienes and their reactions with organolithium reagents".CHEMISTRY-A EUROPEAN JOURNAL 13.22(2007):6484-6494. |
入库方式： OAI收割
来源：化学研究所
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