Replacement of the nitro group by hydrogen

Electrophilic sulfhydration of 8-nitro-cGMP involves sulfane sulfur

“…12,13 At last, the transformation of a nitro group into a thiol moiety has been described, but it occurs through a multi-step reaction mechanism. [14][15][16][17] In this work, we show that H 2 S reacts with 8-nitro-guanosine (8-NO 2 -Gua, used as a model of 8-NO 2 -cGMP) or 8-NO 2 -cGMP. The reaction is inhibited by dioxygen, but it leads to the reduction of the nitro compounds into their corresponding amino analogs, i.e.…”

“…Notes and references ‡ At physiological pH and 25°C, H 2 S dissociates into an equilibrium between H 2 S and HS − , with pK a (H 2 S/HS − ) = 6.97 (the second pK a (HS − /S 2− ) is well above 14). In this paper "H 2 S" refers to the mixture of the two forms obtained by dissolving the salt NaSH in a buffer solution, their respective proportions being fixed by the pH of the buffer.…”

X-philic reactions

“…Moreover, recent investigations reveal the general phenomenon that certain substitution reactions occur as the chain anion-radical processes of the SrnI type. [99][100][101][102][103][104][105][106][107][108][109][110][111] In any case, the SET mechanism is often postulat-ed112-118 on the basis of the structure of the reaction products, but special studies are necessary to distinguish this mechanistic pathway. For example, a clue to the mechanism may be provided by the use of isotopically labeled compounds, as shown in eq 26.30…”

Synthesis, reactions, and applications of fluorine-containing multifunctional carbon compounds

“…Denitration of 32 with n-Bu 3 SnH [44], NaTeH [45], MeSNa [46], and 1-benzyl-1,4-dihydronicotinamide (BNAH) [47] did not give the desired compounds 39 (Scheme 10). Desulfonylation of 32 with Na-Hg [48], BNAH [49], and 1,3-dimethyl-2-phenylbenzimidazole (DMBI) [50] was also unsuccessful [26].…”

“…Dehydronitration using MeSNa [46] was successful for those compounds that contained a benzyl structure, 48f,g. The (Z)-fluoroalkenes 50n,o were produced in a regio-and stereoselective manner in 75 and 55% yields, respectively [26].…”