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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 21
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Original Articles

Conversion of Aldoximes into Nitriles with Raney Nickel in Refluxing 2-Propanol

, , &
Pages 3810-3815 | Received 17 Oct 2007, Published online: 14 Oct 2008
 

Abstract

Aldoximes are readily dehydrated to nitriles with Raney nickel in refluxing 2-propanol.

ACKNOWLEDGMENTS

D. R. Z. gratefully acknowledges financial support a National Science Foundation/Research Site for Educators in Chemistry grant (CHE-9974734) and a Covenant College research grant. R. C. M. gratefully acknowledges financial support from the Research Corporation, the University of Chattanooga Foundation, and the Grote Chemistry Fund. In addition, we are indebted to W. R. Grace Company, Chattanooga, Tennessee, for the generous donation of Raney catalysts.

Notes

a Time to reach complete conversion as determined by GC.

b Isolated yields. Product nitriles were compared to authentic spectra or literature reference spectra and confirmed by 1H NMR and 13C NMR spectroscopy and GC-MS.

c Substrate/Raney nickel, 1/2.5 (w/w).

d Substrate/Raney nickel, 1/5 (w/w).

e Substrate/Raney nickel, 1/7.5 (w/w).

f Product loss observed during rotary evaporation due to volatility of nitrile.

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