I am using triphenylphosphine to convert azide which is bonded to a triazine unit into the corresponding amine but NMR spectrum shows the formation of intermediate which is iminophosphorane (R-N=P(Ph)3). The starting material and this intermediate is not soluble in water. I am facing the difficulty of opening this intermediate to obtained amine structure. If you have any suggestion, please comments.
Best regards
Hi Ferit!
Have you tried stirring your iminophosphorane with a basic solution, 1M NaOH for example?
Good luck!
Hi Leonardo. First of all thank your for your feedback but my compound collapses in the presence of strong bases such as NaOH and also it is not soluble in water. Do you think stirring in a suspension of another base like NaHCO3- works for this purpose ?
Hi Ferit. In my case, after the formation of the iminophosphorane, I simply added diluted HCl. If your compound is not stable in neither acidic nor basic conditions, I suggest you to use trimethylphosphine to reduce the azido compound. The iminophosphorane from this derivative hydrolyses quite easily and you can get rid of it by simply stirring the compound (dissolved in the solvent of choice) with water or in the work-up.
Using trimethylphosphine seems quite reasonable thank you so much Mateus. I will comment the results again after doing experiment :)
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