Sulfur-containing derivatives of 1,4-naphthoquinone, part 1: Disulfide synthesis

Sulfur‐containing derivatives of 1,4‐naphthoquinone, part 2: Sulfenyl derivative synthesis

“…In order to obtain sulfenylchlorides 4a-h, 7, we used amino-, chloro-, thiols 10a-h, 12; synthesis of these compounds has been realized in the two different ways [20]. The reaction was carried out similarly, as described in [22,23], in inert solvents (Scheme 3).…”

“…IR spectra were recorded on Specord M80 in the tablets of KBr. Materials used were disulfides, thiols, and sulfides [20].…”

“…Such a reaction occurred with high yields and without formation of by-products quickly under mild conditions. Sulfenamides have been obtained by an alternative synthesis, which form disulfides [20] and primary, secondary alkyl, and aryl amines in the presence of silver nitrate similar to [27]. Sulfenamide dissolves, and silver mercaptide precipitates (Scheme 6).…”

“…Under long time boiling with excess amount of chlorine or sulfuryl chloride, the decomposition of disulfide and sulfide bonds and chlorination of aromatic ring and in a side chain were observed. One exception was 2,3-disulfenylchloride-1,4-naphthoquinone (2), obtained from bis-disulfide 1 [20] (Scheme 1).…”

Sulfur monochloride in organic synthesis

“…30 In some cases, the reactions of sulfur monochloride with arenes 31 and indoles 13 where R = Ar or Het, n = 1 ± 4; it is clear that such reactions are of no synthetic value.…”