Dearomatizing anionic cyclization and novel skeletal rearrangement: High yield formation of multiply substituted bicyclic or polycyclic spirocyclopentadienes and phenanthrene derivatives from 4-aryl 1-lithio-1,3-butadienes
文献类型：期刊论文
| 作者 | Liu, Lantao; Wang, Zhihui; Zhao, Fei; Xi, Zhenfeng |
| 刊名 | JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2007-04-27 |
| 卷号 | 72期号:9页码:3484-3491 |
| ISSN号 | 0022-3263 |
| DOI | 10.1021/jo070160u |
| 英文摘要 | Both 4-phenyl 1-lithio-1,3-butadienes and 4-naphthyl 1-lithio-1,3-butadienes underwent highly efficient and selective intramolecular nucleophilic addition of the butadienyllithium to the aromatic rings, resulting in full dearomatization of the phenyl rings and partial dearomatization of the naphthyl rings. When the reactions were carried out at lower temperatures, ipso intramolecular nucleophilic attack took place exclusively to afford the spirocyclopentadiene derivatives upon hydrolysis or further treatment with a variety of electrophiles. 4-Naphthyl 1-lithio-1,3-butadienes and 4-phenyl 1-lithio-1,3-butadienes were found to proceed in this reaction under similar conditions, with the former being faster even at -78 degrees C. However, when the reaction of 4-naphthyl 1-lithio-1,3-butadienes was carried out at higher temperatures, such as 75 degrees C, an interesting skeletal rearrangement took place to afford the vicinal attack products, tetrasubstituted phenanthrenes, via a dearomatization/rearomatization process. Mechanistic investigation revealed that the kinetically favored ipso attack intermediates might undergo thermal skeletal rearrangement via 1,2-alkyl shift. |
| 语种 | 英语 |
| WOS记录号 | WOS:000245814900041 |
| 出版者 | AMER CHEMICAL SOC |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/61121]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Xi, Zhenfeng |
| 作者单位 | 1.Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, Beijing 100080, Peoples R China 2.Peking Univ, Coll Chem, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, 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 | Liu, Lantao,Wang, Zhihui,Zhao, Fei,et al. Dearomatizing anionic cyclization and novel skeletal rearrangement: High yield formation of multiply substituted bicyclic or polycyclic spirocyclopentadienes and phenanthrene derivatives from 4-aryl 1-lithio-1,3-butadienes[J]. JOURNAL OF ORGANIC CHEMISTRY,2007,72(9):3484-3491. |
| APA | Liu, Lantao,Wang, Zhihui,Zhao, Fei,&Xi, Zhenfeng.(2007).Dearomatizing anionic cyclization and novel skeletal rearrangement: High yield formation of multiply substituted bicyclic or polycyclic spirocyclopentadienes and phenanthrene derivatives from 4-aryl 1-lithio-1,3-butadienes.JOURNAL OF ORGANIC CHEMISTRY,72(9),3484-3491. |
| MLA | Liu, Lantao,et al."Dearomatizing anionic cyclization and novel skeletal rearrangement: High yield formation of multiply substituted bicyclic or polycyclic spirocyclopentadienes and phenanthrene derivatives from 4-aryl 1-lithio-1,3-butadienes".JOURNAL OF ORGANIC CHEMISTRY 72.9(2007):3484-3491. |
入库方式： OAI收割
来源：化学研究所
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