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Synthesis 2006(19): 3305-3308  
DOI: 10.1055/s-2006-950225
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Silicon-Catalyzed Conversion of Nitro Compounds into Ketones and Poly(1,3-diketones)

Jih Ru Hwu*a, Thainashmuthu Josephrajana, Shwu-Chen Tsayb
a Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan
b Well-being Biochemical Corporation, Neihu Technology Park, Taipei 114, Taiwan
Fax: +886(3)5721594; e-Mail: jrhwu@mx.nthu.edu.tw;
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Publication History

Received 1 May 2006
Publication Date:
04 September 2006 (online)

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Abstract

The reaction of various secondary nitro compounds with 1.1 equivalents of potassium hydride in 1,4-dioxane and then with 0.10 equivalent of chlorotrimethylsilane gave the corresponding ketones in 62-90% yields. By a similar strategy, poly(1,3-diketones) were synthesized directly from nitroalkenes with sodium ethoxide, potassium hydride, and chlorotrimethylsilane in 1,4-dioxane. The use of chlorotrimethylsilane in a catalytic amount was the key to the success of this transformation; the use of an excess of chlorotri­methylsilane led to poor yields for the same reactions.

Key words

nitro - ketone - poly(1,3-diketone) - Nef reaction - silicon