Hello
Nitrooxy group (nitrate esters) is used in the preparation of vasodilators.
The use of silver nitrate to convert alkyl halides to nitrate esters is very common.
A. McKillop & M. E. Ford used mercury nitrate in organic media, but not repeated by someone else.
Can other nitrate salts be used to convert halides to nitrate esters?
Thanks all.
Emami, Mut orgsynth.student
Hi,
The reason this works is HSAB theory. Soft metals like Ag and Hg like soft halides like Cl, Br, and I (F is hard).
You could try other soft metals, but many are toxic.
What about making a really good leaving group like I or triflate and doing SN2 in polar aprotic with nitrate salts?
Hello Mr.Grice
Some good leaving groups like tosylate ,tms ,.. are good.(base on reported works)
But halids are relatively inert in some reactions .
Use of I as leaving group in allylic position is a Conventional method but problem is cost.
Nucleophilc replacement of NO3/X since Hughes & Ingold is Well known but other cations participation or catalysis is unkown...
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