Synthese und Strukturaufkl�rung von 7-Alkylamino-7-phenyl-8-thioxo-1,2,3,4,5,6-hexathiocanen

Reactions of Benzylamine with Sulfur

“…In eq. 5, the hydrogen sulfide formed in [4] reacts with more sulfur and benzylamine to give benzylammonium polysulfides (one of the final products). Both eqs.…”

“…In eq. 6, the benzylamine polysulfides formed in [4] are proposed to decompose to benzylamine, sulfur, and benzylidenirnine polysulfides as observed experimentally for benzylamine disulfide. Since sulfur and benzylamine are produced in this step, eqs.…”

“…Thus, acetophenone at elevated temperatures gives thioamides (1, 2) but at room temperature (in the presence of 0.25 g atoms of sulfur per mol of ketone) gives a Schiff's base (3). When the quantity of sulfur is increased, the yield of Schiff's base decreases, and at a sulfur to ketone ratio of 8 :1 the heterocyclic compound 8-alkylamino -8 -phenyl-l,2,3,4,5,6-hexathiocane-7-thione (1) results (4,5). Primary amines are RHN to be followed by migration of the functional group or groups along the carbon chain with eventual irreversible oxidation at the end of the chain giving the final product.…”

“…It should be emphasized, however, that eqs. 9-12 offer an equally good alternative to [4] and [5] (see also reference 31). In eq.…”

“…The latter point seems justified since only small amounts of N-benzylidene benzylamine and ammonia were produced from benzylidenirnine tetrasulfide and benzylamine in the presence of lead(I1) oxide, a sulfide ion scavenger. In [4], benzylamine reacts with sulfur to give a benzylamine polysulfide and hydrogen sulfide. This is written as an equilibrium since tetraalkylamine polysulfides are known (30) to react with hydrogen sulfide to give amines and elemental sulfur.…”