1) The reaction mechanism by which 2mol.
p-nitrochlorobenzene is applied with 1mol. Na
2S under the presence of a small amount of Na
2S
2 to form
p,
p′-dinitrodiphenyl sulfide was observed and it was found that the reaction proceeded as far as the formation of
p-nitrothiophenol upon completion of which, the reaction occurrs between this newly formed compound and
p-nitrochlorobenzene. It follows, therefore, that when 1mol.
p-nitrochlorobenzene is used the reaction stops with the formation of
p-nitrothiophenol so that the application of
o,
p-dinitrochlorobenzene easily gives
o,
p,
p′-trinitrodiphenyl sulfide, m.p. 158-160°.
2) Application of Na
2S
3 on
p-nitrochlorobenzene, as in the case of Na
2S
2, gives a mixture of
p,
p′-dinitrodiphenyl disulfide and sulfide although the formation of the latter is much lower than in the case of Na
2S
2.
3) Application of Na
2S to
o-nitrochlorobenzene under the presence of Na
2S
2 hardly formed
o,
o′-dinitrodiphenyl sulfide which showed that the reaction takes a different course from that in the case of (1).
4) Application of Na
2S
2 on
o-nitrochlorobenzene gives solely
o,
o′-dinitrodiphenyl disulfide and no monosulfide is formed. However, it was found that the application of Na
2S
2 on
o,
p-dinitro chlorobenzene gave a small amount of monosulfide as well as
o,
o′,
p,
p′-tetranitrodiphenyl disulfide.
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