醇的分子间亲电O-胺化反应。

Intermolecular electrophilic O-amination of alcohols.

作者信息

Hassner Alfred, Patchornik Guy, Pradhan Tarun K, Kumareswaran R

机构信息

Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel.

出版信息

J Org Chem. 2007 Jan 19;72(2):658-61. doi: 10.1021/jo061900m.

DOI:10.1021/jo061900m

PMID:17221992

Abstract

We report the first examples of an intermolecular electrophilic O-amination of aliphatic alcohols. Thus, the new reagents, fluorenone oxime tosylate, 5a, or mesylate, 5b, permit O-amination of diverse alcohols in the presence of NaH under mild conditions. By following the formation of the resulting oxime ethers, 6, the reaction was shown to be sensitive to steric effects in the alcohol. Furthermore, the presence of an aromatic ring or of a double bond in the alcohol molecule (benzyl, allyl) was found to increase the reaction rate.

摘要

我们报道了脂肪醇分子间亲电O-胺化反应的首例实例。因此，新型试剂芴酮肟对甲苯磺酸盐（5a）或甲磺酸盐（5b）能够在温和条件下，于氢化钠存在的情况下使多种醇发生O-胺化反应。通过追踪生成的肟醚（6）的形成过程，该反应显示出对醇中空间效应敏感。此外，发现醇分子中存在芳环或双键（苄基、烯丙基）会提高反应速率。