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Author: Subject: Diphenyl sulfide from diazonium salts.. ?
kmno4
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[*] posted on 9-1-2009 at 07:30
Diphenyl sulfide from diazonium salts.. ?


That is right - is it possible to obtain Ph2S from diazotized aniline and Na2S (or polysulfide) ?
According to :
http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0238
Ph2Se can be obtained in very similar reacion.
Unfortunately, I cannot find anything about preparing Ph2S in this way...:(
I somebody knows something about appropriate synthetic procedure or reasons why it will not work - please write here ;)
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Nicodem
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[*] posted on 10-1-2009 at 04:22


I could not find such a synthesis using SciFinder, but there are several references where diphenyl sulfide was obtained by the reaction between phenyldiazonium and thiophenoxide ions, for example:
J. Am. Chem. Soc., 51 (1929) 1526–1536. DOI: 10.1021/ja01380a033
Tetrahedron Letters, 26 (1985) 6365-6368.
Berichte der Deutschen Chemischen Gesellschaft, 23 (1890), 2469-2472.
Tetrahedron, 42 (1986) 4007-4016.
Tetrahedron Letters, 29 (1988) 4185-4188.
Journal of Organic Chemistry, 65 (2000) 5600-5608.

I have not checked them, but unfortunately all their graphical abstract seem to indicate that the decomposition of isolated diazonium flouroborates in the presence of sodium thiophenoxide in DMSO or the like was used. I would imagine that if there was ever a failed attempt to direct synthesis of Ph2S from phenyldiazonium and Na2S, it would likely be mentioned somewhere in these references.

[Edited on 10/1/2009 by Nicodem]




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