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Synlett 2007(3): 0505-0506  
DOI: 10.1055/s-2007-968003
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© Georg Thieme Verlag Stuttgart · New York

Sodium Azide (NaN3): A Versatile Reagent in Organic Synthesis

Jian-Jiong Li*
The College of Chemistry & Material Science, Hebei Normal ­University, Shijiazhuang 050016, P. R. of China
e-Mail: organicsynchem@163.com;
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Publication History

Publication Date:
07 February 2007 (online)

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Introduction

Sodium azide is a colorless, odorless, white crystalline solid, which is commercially available and widely used in industry, agriculture, medical practice, and organic ­transformations. It has been used for synthesis of β- and γ-azidoarylketones, [1] dialkylcarbamoyl azides, [2] diphen­ylphosphoryl azides, [3] acyl azides, [4] aryl azides, [5] allyl azides, [6] 1,5-fused tetrazoles, [7] 5-substituted 1H-tetrazoles, [8] 1,2,3-triazoles, [9] 1-aryl 1,2,3-triazoles, [10] 1,4-disubstituted 1,2,3-triazoles, [11] and 1-N-glycosylthio­methyl-1,2,3-triazoles. [12] In addition, sodium azide has been widely employed for preparation of α-azido­ketones, [13] 1-aryl-1H-benzotriazoles, [14] 3-cyanoindoles, [15] and Fmoc-protected amino alcohols, [16] as a suitable ­nucleophile for the Michael-induced ring closure of 2-bromoalkylidene­malonates to 3,3-dialkyl-2-azidocyclopropane-1,1-dicarboxylates. [17]