atomicfire - 3-5-2011 at 06:45
Is it possible to run a diazotization directly from a nitroso group?
Or how would one reduce it to the amine?
smuv - 3-5-2011 at 06:57
yes
atomicfire - 3-5-2011 at 07:48
What is the mechanism for such a reaction?
smuv - 3-5-2011 at 13:31
It can be done by HCl in ethanol using an excess of ethyl nitrite but only with electron rich nucleuses. I cannot be sure of the mechanism but
something along the lines of reduction of the nitroso cpd under the reaction conditions (probably by oxidizing the ethyl nitrite to acetaldehyde) to
the amine followed by standard sandmeyer diazotization.
See Ref.
Attachment: diazonium_salts_directly_via_EtONO.pdf (134kB)
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AndersHoveland - 3-5-2011 at 13:34
I would wonder whether cold (>5C) nitrosobenzene reacting with a solution of chloramine would form the diazo chloride salt.
I was not able to find out about diazotizations, but did find some interesting related reactions:
Diazotization of (C6H5)NHCH3 forms the nitrosamine (where the hydrogen on the nitrogen atom is replaced by a nitroso group --N=O )
Diazotization of (C6H5N(CH3)2 puts a nitroso group in the 4-position (on the far opposite side) on the benzene ring, forming ON--C6H4--N(CH3)2
Reaction of nitrosobenzene (C6H5NO) with hydroxylamine-O-suphonic acid (NH2OSO3H) gave phenyl azide (C6H5N3)
http://docs.google.com/viewer?a=v&q=cache:wdiIieXw8MQJ:p...