Aluminium azide

Leffler, f. E., and L. J, Todd Reaction of Dimesitylboron Fluoride with Aluminium Azide. Chem. and Ind. 1961, 512. 

A standard literature method [1,2] had been used frequently and uneventfully to prepare the azide from trimethylsilyl chloride and sodium azide in presence of aluminium chloride as catalyst. A recent duplication led to a violent detonation during distillation of the product, and this was attributed to carry-over of traces of aluminium azides into the distillation flask. Precautions are detailed [3]. 

The scope of this reaction (Scheme 16) has been extended to other 5-substituted tetrazoles, readily prepared by the reaction of nitriles with aluminium azide <2002J(P1)1543>. Using triphenylphosphine under mild conditions, the resulting dithiazolimines 169 are rapidly converted into cyanothiadiazoles 170 in high yield (Equation 61 and Table 10). 

Acetyl-4-(4/-sulfophenyl)-3-tetrazene, 2982 Aluminium azide, 0082 Aluminium tetraazidoborate, 0059 Amino guanidine, 0507 1-Amino-3-nitroguanidine, 0495 5-Aminotetrazole, 0461 5-Amino-l,2,3,4-thiatriazole, 0413... 

This large and well documented group of explosive compounds contains some which are widely used industrially [1]. The text gives a thorough treatment of all aspects of the physics and chemistry (Vol. 1) and of the applications (Vol. 2) of this important group of energetic compounds [2] and individually indexed compounds are Aluminium azide, 0082... 

P. A. M. van der Klein, W. Filemon, G. H. Veeneman, G. A. van der Marel, and J. H. van Boom, Highly regioselective ring opening of five-membered cyclic sulfates with lithium aluminium azide synthesis of azido sugars, J. Carhohydr. Chem., 11 (1992) 837-848. 

A peculiar reaction of the terminal nitrogen in a carbamoyl azide is the conversion of phenylcarbamoyl azide to l-phenyltriazolin-5-one under the influence of aluminium azide... 

A reaction of phenylcarbamoyl azide with aluminium azide 2" has been mentioned above (section II.B). 

In 1999, Jacobsen reported on a catalytic asymmetric conjugated addition of hydrazoic acid to unsaturated imide derivatives (Equation 4.1). This breakthrough was possible through the use of aluminium salen azide complex 1 as catalyst. The reaction proceeded in excellent yields and enantioselectivities for alkyl substituted acceptors. Two mechanisms were proposed for this reaction activation of the azide as an aluminium azide as shown by Chung and co-workers or Lewis acid activation of the imide. The first-order dependence of the rate law on catalyst 1 indicated that dual activation was improbable. In 2005, Jacobsen reported on the extension of this methodology to ,j8-unsaturated ketones. 

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