monochemist - 6-9-2006 at 01:20
Hi,
I need help with the synthesis methods of diphenyl ethers and thio ethers, or phenoxyphenol and its thio analogue, is it possible to prepare it using
diazonium salt and then coupling. what would be the conditions of the reaction? as using diazonium salt will enable the use of substituted rings in
the reaction.
thanks,
bye
solo - 6-9-2006 at 03:20
SYNTHESIS OF AROMATIC ETHERS UNDER MICROWAVE IRRADIATION IN DRY MEDIA.
DARIUSZ BOGDAL*, JAN PIELICHOWSKI, and ADAM BORON
http://www.cyf-kr.edu.pl/~pcbogdal/phenol/
Abstract:
Under microwave irradiation a number of phenols react remarkably fast with a number of primary alkyl halides to give aromatic ethers. The procedure
is alternative to those which rely on the use of dipolar aprotic solvents, sodium, sodium hydride, sodium amide and several procedure that rely on
"standard" PTC methods
[Edited on 6-9-2006 by solo]
Attachment: SYNTHESIS OF AROMATIC ETHERS UNDER MICROWAVE IRRADIATION IN DRY MEDIA..pdf (75kB)
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Nicodem - 6-9-2006 at 06:16
Solo, you misunderstood the question. He is asking about the synthesis of diaryl ethers which obviously can’t be made by alkylation.
I don’t think diazonium salts couple with phenols to give diaryl ethers, they give diazo compounds instead. At the moment I can remember any method
except for the Ullman (aka Goldberg) reaction of phenolates/thiophenolates with iodo- or bromoaryls.
monochemist - 11-9-2006 at 05:23
Exactly Nicodem, but thank s for both of you for the contribution, but concerning the coupling with diazonium, I think it is possible as I have found
a chemical compound which is used as a pesticide; it is based on a thio ether and on one of the two rings bears three chlorine atoms and also I found
a compound which is considered as the intermediate and the later was formed as a diazonium compound which confirm my view that using diaonium salts
and then coupling we can reach to a multi-substituted (halogenated) di aryl ethers, but using the Ullman reaction is very difficult to control the
substitution position and also I do not know what would be the situation for the yield.
I hope someone can help, plssssssssss