Replacement of other elements by sulfur groups

Organic sulfides are obtained by treating quaternary ammonium salts with sodium sulfide, the corresponding tertiary amines being by-products. The reaction is, however, smooth only if a benzyl or an allyl group is present as well as an aryl group, since only the two first are transferable for alkylation of sodium sulfide.491 

One nitro group of 0-dinitrobenzene and its derivatives is reactive and can be replaced by a mercapto, alkylthio, or sulfo group under the influence of sodium sulfide, sodium thiolates, or sodium sulfite, respectively. For preparative purposes this reaction is, however, restricted to a few examples. o-Dinitro-benzene and sodium sulfide give bis-(0-nitrophenyl) sulfide,492 and trinitro-anisole gives the bis(methoxydinitrophenyl) sulfide.493 

Replacement of the nitro group by a sulfo group is particularly easy in the nitroanthraquinone series, when these compounds are boiled for several hours with sodium or potassium sulfite in aqueous solution.495,496 

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