kmno4
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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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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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unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
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