Categories: N/N Bond Formation >
Synthesis of Azides
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Recent Literature

Imidazole-1-sulfonyl azide hydrochloride equals triflyl azide in its ability to
act as a “diazo donor” in the conversion of both primary amines into azides and
activated methylene substrates into diazo compounds. Crucially, this reagent can
be prepared in a one-pot reaction on a large scale from inexpensive materials,
is shelf-stable and is conveniently crystalline.
E. D. Goddard-Borger, R. V. Stick, Org. Lett., 2007,
9, 3797-3800.

The synthesis of aromatic azides from the corresponding amines is
accomplished under mild conditions with tert-butyl nitrite and
azidotrimethylsilane. 1,4-Disubstituted 1,2,3-triazoles were obtained in
excellent yields from various aromatic amines without the need for isolation of
the azide intermediates.
K. Barral, A. D. Moorhouse, J. E. Moses, Org. Lett., 2007,
9, 1809-1811.

Aliphatic and aromatic aldehydes
gave acyl azides by reaction with iodine azide at 0 - 25°C. If the reaction
is performed at reflux Curtius rearrangement occurs and carbamoyl azides are
obtained directly from the aldehyde in 70-97% yield.
L. Marinescu, J. Thinggaard, I. B. Thomsen, M. Bols,
J. Org. Chem., 2003, 68, 9453-9455.
