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DOI: 10.1055/s-2004-831254
Nicotinoyl Azide (NCA)-Mediated Mitsunobu Reaction: An Expedient One-Pot Transformation of Alcohols into Azides
Publication History
Publication Date:
07 October 2004 (online)
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Abstract
A practical and simple method that allows preparation of azides from alcohols is described. The process involves oxyphosphonium-type activation and it is based upon the use of nicotinoyl azide (NCA), a cheap and easily accessible azide ion source.
Key words
azides - alcohols - nicotinoyl azide (NCA)
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References
DSC (Mettler-Toledo Star® System, heating rate: 10 °C min-1): endothermic effect between 40 °C and 66 °C (melting of the reagent, ΔHendo = 106 J g-1); exothermic effect between 73 °C and 151 °C (Schmidt rearrangement plus decomposition, ΔHexo = 1051 J g-1).
421H NMR (300 MHz, CDCl3): δ = 1.24-1.31 (m, 6 H), 4.15-4.27 (m, 4 H), 7.35-7.42 (m, 1 H), 7.96-7.98 (d, J = 7.6 Hz, 1 H), 8.71-8.73 (d, J = 5 Hz, 1 H), 8.86 (s, 1 H). MS m/z = 282.26 (MH+).