芳基硫醚与烯丙基腈的串联[5,5]-/[3,3]-重排反应

Synthesis Pub Date : 2024-06-05 DOI:10.1055/a-2338-9005
Mengjie Hu, Liying Ru, Mengjiao Zhu, Shengwen Yang, Suojiang Fan, Jiangtao Ji, Dingming Zheng, Bo Peng
{"title":"芳基硫醚与烯丙基腈的串联[5,5]-/[3,3]-重排反应","authors":"Mengjie Hu, Liying Ru, Mengjiao Zhu, Shengwen Yang, Suojiang Fan, Jiangtao Ji, Dingming Zheng, Bo Peng","doi":"10.1055/a-2338-9005","DOIUrl":null,"url":null,"abstract":"Tandem aromatic rearrangements can redirect the regioselectivity of original rearrangement and increase the complexity of products. Despite their obvious synthetic value, only few protocols of tandem aromatic rearrangements are reported. In this Article, we describe two new tandem aromatic rearrangements by using sulfonium rearrangements. Specifically, [5,5]-rearrangement of phenyl sulfoxides with allyl nitriles followed by [3,3]-Cope rearrangement forges the tandem [5,5]-/[3,3]-rearrangements which affords ortho-functionalized phenyl sulfides as products. The other tandem rearrangement proceeds through [5,5]-rearrangement of phenyl sulfoxides with allyl nitriles and the subsequent nuclephilic addition/DDQ-oxidation induced [3,3]-Cope rearrangement, which eventually achieves meta-functionalized phenyl sulfides as products.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"58 7","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Tandem [5,5]-/[3,3]- rearrangements of aryl sulfoxides with allyl nitriles\",\"authors\":\"Mengjie Hu, Liying Ru, Mengjiao Zhu, Shengwen Yang, Suojiang Fan, Jiangtao Ji, Dingming Zheng, Bo Peng\",\"doi\":\"10.1055/a-2338-9005\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Tandem aromatic rearrangements can redirect the regioselectivity of original rearrangement and increase the complexity of products. Despite their obvious synthetic value, only few protocols of tandem aromatic rearrangements are reported. In this Article, we describe two new tandem aromatic rearrangements by using sulfonium rearrangements. Specifically, [5,5]-rearrangement of phenyl sulfoxides with allyl nitriles followed by [3,3]-Cope rearrangement forges the tandem [5,5]-/[3,3]-rearrangements which affords ortho-functionalized phenyl sulfides as products. The other tandem rearrangement proceeds through [5,5]-rearrangement of phenyl sulfoxides with allyl nitriles and the subsequent nuclephilic addition/DDQ-oxidation induced [3,3]-Cope rearrangement, which eventually achieves meta-functionalized phenyl sulfides as products.\",\"PeriodicalId\":501298,\"journal\":{\"name\":\"Synthesis\",\"volume\":\"58 7\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-06-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthesis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2338-9005\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2338-9005","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

摘要

串联芳香重排可以改变原始重排的区域选择性,并增加产物的复杂性。尽管串联芳香重排具有明显的合成价值,但目前有关串联芳香重排的报道却很少。在本文中,我们介绍了利用锍重排进行的两种新的串联芳香重排。具体来说,苯硫醚与烯丙基腈发生[5,5]-重排,然后发生[3,3]-Cope 重排,形成串联[5,5]-/[3,3]-重排,生成正交官能化的苯硫化物作为产物。另一种串联重排是通过苯硫醚与烯丙基腈的[5,5]-重排,以及随后亲核加成/DDQ-氧化诱导的[3,3]-Cope 重排,最终得到元官能化的苯硫醚作为产物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Tandem [5,5]-/[3,3]- rearrangements of aryl sulfoxides with allyl nitriles

Tandem [5,5]-/[3,3]- rearrangements of aryl sulfoxides with allyl nitriles
Tandem aromatic rearrangements can redirect the regioselectivity of original rearrangement and increase the complexity of products. Despite their obvious synthetic value, only few protocols of tandem aromatic rearrangements are reported. In this Article, we describe two new tandem aromatic rearrangements by using sulfonium rearrangements. Specifically, [5,5]-rearrangement of phenyl sulfoxides with allyl nitriles followed by [3,3]-Cope rearrangement forges the tandem [5,5]-/[3,3]-rearrangements which affords ortho-functionalized phenyl sulfides as products. The other tandem rearrangement proceeds through [5,5]-rearrangement of phenyl sulfoxides with allyl nitriles and the subsequent nuclephilic addition/DDQ-oxidation induced [3,3]-Cope rearrangement, which eventually achieves meta-functionalized phenyl sulfides as products.
求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
自引率
0.00%
发文量
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信