Synthesis of α-Siloxyamides by the Reaction of a Carbamoylsilane with Ketones

doi:10.6023/cjoc201404048

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (10): 2124-2129.DOI: 10.6023/cjoc201404048 Previous Articles Next Articles

Notes

氨甲酰基硅烷与酮反应合成α-硅氧基酰胺衍生物

姚远^a,b, 李伟东^a, 陈建新^a

a. 山西师范大学化学与材料科学学院临汾 041004;
b. 山西省临汾市实验中学临汾 041000

收稿日期:2014-04-25 修回日期:2014-05-21 发布日期:2014-06-16
通讯作者: 陈建新 E-mail:jjxxcc2002@yahoo.com
基金资助:
山西省留学回国人员基金（No. 0713）、山西省自然科学基金（No. 2012011046-9）、山西师范大学基金（No. SD2012CXSY-11）资助项目.

Synthesis of α-Siloxyamides by the Reaction of a Carbamoylsilane with Ketones

Yao Yuan^a,b, Li Weidong^a, Chen Jianxin^a

a. College of Chemistry and Material Science, Shanxi Normal University, Linfen 041004;
b. The First Experimental Middle School of Linfen City, Linfen 041000

Received:2014-04-25 Revised:2014-05-21 Published:2014-06-16
Supported by:
Project supported by the Foundation for Returness Overseas Scientists of Shanxi Province (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Foundation of Shanxi Normal University (No. SD2012CXSY-11).

1. Synthesis of α-Siloxyamides by the Reaction of a Carbamoylsilane with Ketones.PDF(162KB)

Abstract

Under using anhydrous toluene as a solvent, N,N-dimethyl carbamoyl(trimethyl)silane reacted with a series of aryl ketones or unsaturated aryl ketones at 105 ℃ to afford α-siloxyamide derivatives in good yields (60%～89%). The structures of the products were characterized by element analysis, ¹H NMR, ¹³C NMR and IR spectra. The alkyl ketones including the alkyl-aryl ketones and alkyl-unsaturated ketones poorly reacted with N,N-dimethylcarbamoyl(trimethyl)silane. The experimental results showed that the electronic property of the substituted group on the aryl ring strongly affected the reaction. In the case of the aryl ketones with stronger donor group on the aryl ring, the longer time was needed for the reaction.

Key words: carbamoylsilane, ketones, α-siloxyamides, nucleophilic addition, synthetic methods

Cite this article

Yao Yuan, Li Weidong, Chen Jianxin. Synthesis of α-Siloxyamides by the Reaction of a Carbamoylsilane with Ketones[J]. Chin. J. Org. Chem., 2014, 34(10): 2124-2129.

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氨甲酰基硅烷与酮反应合成α-硅氧基酰胺衍生物

Synthesis of α-Siloxyamides by the Reaction of a Carbamoylsilane with Ketones

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