Described is a process for converting an alcohol to an azide with SN2 inversion using a phosphoryl azide, e.g. diphenylphosphoryl azide (DPPA). Good yields of azide in high enantiomeric excess can be achieved specifically for benzylic alcohols and alpha-hydroxy alkyl esters.

A list of typical conditions for the conversion of an alcohol to an azide. The presence of a keto group in the molecule does not interfere with azide formation.

This synthesis of azide is more convenient than the traditional route (alcohol-osylate-*azide) which is longer and also prone to a]icene formation.
Example 2. Good yields of azide in high enantiomeric excess can be achieved specifically for benzylic alcohols and alpha-hydroxy alkyl esters. The process is carried at preferably room temperature in an inert dry aprotic solvent, e.g. diphenylphosphoryl azide (DPPA). Azide is the anion with the formula N − 3.It is the conjugate base of hydrazoic acid (HN 3).N − 3 is a linear anion that is isoelectronic with CO 2, NCO −, N 2 O, NO + 2 and NCF.Per valence bond theory, azide can be described by several resonance structures; an important one being − = + = −.Azide is also a functional group in organic chemistry, RN 3.. Described is a process for converting an alcohol to an azide with S N 2 inversion using a phosphoryl azide, e.g. To a solution of the SM (3.1 g, 16.2 mmol) in THF (60 mL) at 0 C was added DIAD (6.3 mL, 32.0 mmol), PPh3 (8.52 g, 32.5 mmol), and DPPA (6.98 mL, 32.5 mmol).

Initially to optimize the conversion of benzyl alcohol to benzyl azide, we tried the reaction under solvent-free conditions and in different solvents such as water, acetonitrile, and dichloromethane and under different temperatures including 60, 80, 100, and 120 °C for evaluating the acidity and applications of this Brönsted acid.

One Pot Conversion of Alcohols to Amines Synth Commun 30(12), 2233-2237 (2000) ... Alternatively they can be prepared by a two step methodology : a) conversion of alcohol to azide by Mitsunobu reaction using hydrazoic acid, triphenylphosphine and diethylazodicarboxylate (DEAD) 4 , b) reduction of azide to amine. The process is carried at preferably room temperature in an inert dry aprotic solvent, e.g. 1. A practical one-pot synthesis of azides directly from alcohols ... Alcohol; azide; triphenylphosphine; iodine; imidazole; chemoselective.


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