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Synlett 2007(13): 2144-2145  
DOI: 10.1055/s-2007-984895
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© Georg Thieme Verlag Stuttgart · New York

Trimethylsilyl Azide (TMSN3): A Versatile Reagent in Organic Synthesis

Mohammad Jafarzadeh*
School of Chemical Science, Universiti Sains Malaysia, 11800 Minden, Penang Island, Malaysia
e-Mail: m_jafarzadeh@chemist.com;
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Publication History

Publication Date:
12 July 2007 (online)

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Trimethylsilyl Azide (TMSN3): A Versatile Reagent in Organic SynthesisSynlett 2007; 2007(13): e1-e1
DOI: 10.1055/s-2007-985564

Introduction

In recent times, azides have received much attention in synthetic organic chemistry. The azide moiety is a versatile functional group that serves many purposes in organic synthesis and azides can react very differently under different reaction conditions. In spite of their less-attractive properties (explosiveness, toxicity), a plethora of new ­applications has been published. [1] Silyl azides are valuable reagents in organic synthesis because they have, unlike sodium azide and hydrogen azide, no immediate explosive properties. However, they hydrolyze in the long term to the volatile, toxic, and explosive hydrogen azide and therefore must be stored in the absence of moisture and acids. Trimethylsilyl azide (Me3SiN3; bp 95 ºC), which is also commercially available, can be prepared from tri­methylsilyl chloride by reaction with sodium azide in ­diglyme. [2]

In the last years, there has been growing interest in this compound that has been used as a fruitful reagent for synthesis of triazoles, [3] tetrazoles, [4] glycosyl azides, [5] β-silyl azides, [6] azirines, [7] nitriles, [8] for β-azidation of α,β-unsaturated carbonyl compounds, [9] carboazidation of ­allenes, [10] azidophenylselenylation of glycals, [11] ring ­opening of aziridines, [12] oxazolines, [13] and epoxides. [14]