Electronic spectra of some aromatic mercury compounds

Synthesis of a New Class of Highly Functionalised Benzamides by Threefold Sequential Nucleophilic Substitution at a Resin-Bound Polyelectrophile

“…As indicated earlier, we anticipated that treatment of resin‐bound 4‐amino‐2‐nitro‐5‐sulfonylbenzamides 14 with various amines should result in substitution of the nitro group. We were, however, aware that it might be difficult to predict whether the nitro group or the sulfonyl group would be displaced,9 and also that it might be a problem to obtain complete conversion without using very high temperatures 11. To our delight, however, treatment of 14 with a 2 M solution of primary or secondary aliphatic amines in NMP at 100 °C resulted in clean substitution of the nitro group, and complete conversion could be obtained by repeating the treatment twice (Scheme ).…”

“…Achievement of a third nucleophilic aromatic substitution requires displacement of the nitro group, which is normally only seen when the nitro group is activated by another nitro group in the ortho or the para position 10. It has also been reported that a nitro group activated by a sulfonyl group in the para position was displaced by piperidine at 200 °C 11. The search for a way to achieve threefold sequential nucleophilic substitution at a resin‐bound 4,5‐difluoro‐2‐nitrobenzamide is therefore a matter of controlling the regiochemistry and achieving displacement of the nitro group without employing too harsh conditions.…”

Arylmercury Compounds. Part VI. Asymmetric Diarylmercury Compounds

“…IR and PMR spectra are identical to the ones obtained for an equimolar mixture of the two symmetric compounds. Based on the nature of known asymmetric organometallic compound [10], it is only reasonable to assume that IR and PMR spectra would not show a remarkable difference between an asymmetric product and an equimolar mixture of the two symmetrical ones.…”

Reactions of aromatic radical anions. 13. Contributing factors for the partitioning reaction of sodium naphthalene with phenylacetonitrile

“…The absence of amine products contrasts with the reduction using sodium in ethanol. 17 The mechanism of both amine formation and reductive elimination of cyanide are thought to proceed via a nitrile radical anion.…”