Preparation and Electronic Spectra of Mercaptoacetamides

Abstract

A new method for preparing 2‐mercaptoacetamide and N‐alkyl‐2‐mercaptoacetamides has been described. Electronic spectra of sixteen N‐alkyl and N‐aryl‐2‐mercaptoacetamides have been compared with corresponding substituted acetamides and discussed. The results reveal the possibility of an intra‐molecular hydrogen‐bonding between NH hydrogen and sulphur of SH group.

On the Chalcogenophilicity of Mercury: Evidence for a Strong Hg−Se Bond in [TmBut]HgSePh and Its Relevance to the Toxicity of Mercury

“…Combustion analyses were carried out by Robertson Microlit Laboratories, Madison, NJ, USA. PhN(H)C(O)CH 2 SH,63 [Tm Bu t ]HgBr,28 [Tm Bu t ]HgEt,10 [Tm Bu t ]HgSPh10 and [Tm Bu t ]ZnSePh17 were synthesized as previously reported. CAUTION: All mercury compounds are toxic and appropriate safety precautions must be taken in handling these compounds .…”

Thiolate exchange in [TmR]ZnSR′ complexes and relevance to the mechanisms of thiolate alkylation reactions involving zinc enzymes and proteins

“…IR spectra were recorded as KBr pellets and are reported in cm À1 ; w = weak, m = medium, s = strong, vs = very strong. N-phenyl-2-mercaptoacetamide, PhN(H)C(O)CH 2 SH [77], [Tm Ph ]ZnSPh [44], [Tm Ph ]ZnSCH 2 C(O)N(H)Ph [69], ½Tm Bu t ZnMe [45], ½Tm Bu t CdMe (Melnick, Parkin, unpublished results) and [Tm Bu t ]ZnSPh [45], were obtained by the literature methods. …”

Additions to alkenes via metal ion-promoted oxidation of dialkyl and diaryl disulphides

“…These structures are assigned on the basis of the relative chemical shifts of the methylene and methine protons proximate to the heteroatoms in the adducts. Confirmation of formation of a single regioisomer in the case of compound (8) was obtained by hydrolysis to give the single hydroxysulphide (12) which was characterised spectroscopically. Our results closely accord with the stereochemical and regiochemical outcome of analogous examples reported by Trost,' but in addition to hept-1-ene an anti-Markownikoff product was observed as a minor adduct.…”

“…With diphenyl disulphide it is possible to achieve satisfactory conversions into acetamidosulphides. Thus the pure trifluoroacetoxysulphide (8) gives the acetamidosulphide (13) in 70% yield under Ritter conditions. Although the conversions of the pure trifluoroacetoxysulphides into acetamidosulphides 15) and ( 5)] from dibenzyl disulphide.…”

“…Further purification by column chromatography (silica gel, eluant light petroleum) afforded, as an oil, trans-1 -phenylthio-2-trijluoroacetoxycyclohexane (1) (1.30 complex); 6, 23.1, 24.5, 30.3, 31.6,49.7, 79.2, 127.1, 127.8, 129.0, 129.1, 132.4, and 133.2 p.p.m. 1 -Phenylthio-2-trijluoroacetoxyoctane (8). Diphenyl disulphide (1.1 1 g) was oxidised by lead tetra-acetate (2.4 g) in the presence of oct-1-ene (8.83 g) by the above procedure.…”