Solvent effect on the reversibility of base catalyzed Henry reactions : Triton B catalyzed nitro aldol reactions in alcohol

F. Ono, Hiroe Soejima, J. Tanaka, S. Kanemasa
{"title":"Solvent effect on the reversibility of base catalyzed Henry reactions : Triton B catalyzed nitro aldol reactions in alcohol","authors":"F. Ono, Hiroe Soejima, J. Tanaka, S. Kanemasa","doi":"10.15017/14601","DOIUrl":null,"url":null,"abstract":"The amine catalyzed nitro aldol reactions between nitromethane and aldehydes are found to be reversible in an alcohol solvent on the basis of the reaction monitoring by 1H NMR spectroscopy. The reaction in alcohols is particularly rapid to complete the equilibrium in a short period of time at room temperature, producing nitro aldol product in high yields. Triton B is especially effective as catalyst in the nitro aldol reactions of nitromethane in methanol. Only a small catalytic loading of triton B as small as 1 mol% is enough to finish the reaction. Aromatic, aliphatic, and {alpha},{beta}-unsaturated aldehydes as well as aldehyde hydrates and aqueous aldehydes are successfully employed.","PeriodicalId":11722,"journal":{"name":"Engineering sciences reports, Kyushu University","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2008-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Engineering sciences reports, Kyushu University","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.15017/14601","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

Abstract

The amine catalyzed nitro aldol reactions between nitromethane and aldehydes are found to be reversible in an alcohol solvent on the basis of the reaction monitoring by 1H NMR spectroscopy. The reaction in alcohols is particularly rapid to complete the equilibrium in a short period of time at room temperature, producing nitro aldol product in high yields. Triton B is especially effective as catalyst in the nitro aldol reactions of nitromethane in methanol. Only a small catalytic loading of triton B as small as 1 mol% is enough to finish the reaction. Aromatic, aliphatic, and {alpha},{beta}-unsaturated aldehydes as well as aldehyde hydrates and aqueous aldehydes are successfully employed.
溶剂对碱催化Henry反应可逆性的影响:Triton B在醇中催化硝基醇反应
通过1H NMR监测,发现胺催化硝基甲烷与醛之间的硝基醛反应在醇溶剂中可逆。该反应在醇类中的反应速度特别快,在室温下可在短时间内完成平衡,产率高。在硝基甲烷在甲醇中的硝基醇反应中,Triton B是特别有效的催化剂。只需要少量的triton B催化负荷(1mol %)就足以完成反应。芳香族,脂肪族,和{α},{β}-不饱和醛以及醛水合物和水醛被成功地使用。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
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