SPECIALTOPIC	Synthesis 2006: 3305-3308   DOI: 10.1055/s-2006-950225
© 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;
Received 1 May 2006

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