1949 年 69 巻 12 号 p. 557-560
1) The reaction mechanism by which 2mol. p-nitrochlorobenzene is applied with 1mol. Na2S under the presence of a small amount of Na2S2 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 Na2S3 on p-nitrochlorobenzene, as in the case of Na2S2, gives a mixture of p, p′-dinitrodiphenyl disulfide and sulfide although the formation of the latter is much lower than in the case of Na2S2.
3) Application of Na2S to o-nitrochlorobenzene under the presence of Na2S2 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 Na2S2 on o-nitrochlorobenzene gives solely o, o′-dinitrodiphenyl disulfide and no monosulfide is formed. However, it was found that the application of Na2S2 on o, p-dinitro chlorobenzene gave a small amount of monosulfide as well as o, o′, p, p′-tetranitrodiphenyl disulfide.