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NacNacAl 与二苯甲酮的加合物及其偶联化学。

Adduct of NacNacAl with Benzophenone and Its Coupling Chemistry.

机构信息

Department of Chemistry, Brock University, 1812 Sir Isaac Brock Way, St. Catharines, ON, L2S 3A1, Canada.

Department of Chemistry & Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, ON, L8S 4L8, Canada.

出版信息

Chemistry. 2020 Jan 2;26(1):206-211. doi: 10.1002/chem.201903719. Epub 2019 Nov 12.

DOI:10.1002/chem.201903719
PMID:31559656
Abstract

Reaction of NacNacAl (NacNac=[DippNC(Me)CHC(Me)NDipp] ) with one equivalent of benzophenone affords a ketylate species NacNacAl(η (C,O)-OCPh ) that undergoes easy cyclization reactions with unsaturated substrates. The scope of substrates included benzophenone, aldimine (PhNC(Ph)H), quinoline, phenyl nitrile, trimethylsilyl azide, and a saturated cyclic thiourea. The latter substrate reacted by an unusual C-N cleavage that left the C=S functionality intact. The new products were characterized by NMR spectroscopy and X-ray diffraction analysis.

摘要

NacNacAl(NacNac=[DippNC(Me)CHC(Me)NDipp])与等当量的二苯甲酮反应生成酮化物 NacNacAl(η(C,O)-OCPh),该酮化物易与不饱和底物发生环化反应。底物的范围包括二苯甲酮、亚胺(PhNC(Ph)H)、喹啉、苯腈、三甲基硅基叠氮化物和饱和环状硫脲。后一种底物发生了不寻常的 C-N 断裂反应,C=S 官能团保持完整。新产物通过 NMR 光谱和 X 射线衍射分析进行了表征。

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