Tetrahedron p. 1163 - 1168 (1982)
Update date:2022-07-30
Topics:
Joergensen, K. A.
Ghattas, A.-B.A.G.
Lawesson, S.-O.
The reaction of NaNO2 in acidic solution with thiocarbonyl compounds has been studied.Secondary- and tertiary thioamides, 1-benzyl-hexahydro-2H-azepine-2-thione, 5-ethyl-5-phenyl thiobarbituric acid, certain thiourea derivatives, 2H-1-benzopyran-2-thione, O,O-diphenyl-thiocarbonic ester, O,S-diphenyl-dithiocarbonic ester, N,N-dimethyl-S-phenyl-dithiocarbamatic ester, N-ethyl-N-phenyl-O-ethyl-thiocarbamatic ester are all converted into the corresponding carbonyl-analogues. 4,4'-Bis(dimethylamino)-thiobenzophenone (Michler's thioketone) gives 3-nitro-4,4'-bis(dimethylamino)-benzophenone at room temperature.At (-10 deg C)-(-5 deg C) the expected oxo compound is obtained as the main product together with 4-(N-nitroso-methylamino)-4'-(dimethylamino)-benzophenone.
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Doi:10.1016/S0040-4039(00)88588-3
(1982)Doi:10.1007/BF00598592
(1988)Doi:10.1021/jo00150a026
(1983)Doi:10.1002/hlca.19820650615
(1982)Doi:10.1039/c4dt02366h
(2014)Doi:10.1055/s-1982-29942
(1982)