Chemistry of the sulfur-nitrogen bond. VI. Convenient one-step synthesis of sulfenimines (S-aryl thiooximes)

Davis, Franklin A.; Slegeir, W.; Evans, S. A.; Schwartz, Anne C.; Goff, David L.; Palmer, Robert C.

doi:10.1021/jo00956a016

Cited by 56 publications

(21 citation statements)

References 3 publications

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“…Chiral sulfenylimines are widely applied in asymmetric synthesis as a source of chirality . Sulfenylimines 132 were obtained by Davis et al in the second half of the 20th century from disulfides 130 , carbonyl compounds 131 , and ammonia through the action of silver nitrate (Scheme ) …”

Section: Synthesis Of Sulfenyliminesmentioning

confidence: 99%

Oxidative Coupling with S–N Bond Formation

2018

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Oxidative strategies are a powerful tool in organic synthesis for the formation of heteroatom–heteroatom, carbon–heteroatom, and carbon–carbon bonds. Among these processes the reactions of oxidative S–N bond formation deserve considerable interest as convenient, effective, and environmentally friendly alternatives to existing methods for the synthesis of a great variety of organic compounds widely used in organic and medicinal chemistry. These transformations take place through the interaction of S‐ and N‐reagents and an oxidant, by radical or ionic mechanisms. Sulfinic acids and their salts, thiols, sulfonyl hydrazides, and thiosulfonates are generally used as S‐reagents; aliphatic and aromatic amines are usually applied as N‐reagents. The role of the oxidant mostly lies in the oxidation of the S‐reagent, after which the formed active species reacts with the N‐reagent to result in the S–N coupling product. There are two versions of oxidative S–N coupling processes: the intermolecular variant opens simple pathways to sulfen‐, sulfin‐, and sulfonamides, sulfenyl‐ and sulfoximines, sulfanes, and sulfur diimides, whereas the intramolecular one leads to the formation of various heterocycles. Of the major problems associated with successful performance of oxidative S–N coupling reactions, the first relates to the search for coupling partners that will work together to form a new bond under oxidative conditions. The second is the choice of a suitable oxidative system that will not overoxidize starting compounds. That is why mild oxidants, such as hypervalent iodine compounds and copper salts and complexes, are generally applied in these processes. This is the first exhaustive review relating to achievements in oxidative transformations involving S–N bond formation. It summarizes 134 references, mainly from 2000 to 2018, and is divided into chapters according to the classes of compounds synthesized.

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Section: Synthesis Of Sulfenyliminesmentioning

confidence: 99%

Oxidative Coupling with S–N Bond Formation

2018

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“…The preparative removal of the p toluenesulfinyl fragment is also possible under the action of the Dess-Martin reagent (72-76%) [12] or excess of MeMgBr (70-95%) [13,14]. N Sulfenyl imines result from the condensation of aldehydes and ketones with sulfenamides [16] or aryl disulfides and ammonia in the presence of AgNO 3 [17]; N sulfenyl ketimines are also obtained from ketoximes and secondary nitro compounds [18].…”

Section: N Sulfinyl Imines (I)mentioning

confidence: 99%

Stable synthetic equivalents of N-unsubstituted imines: Part 1. Synthesis

et al. 2012

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“…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).…”

Section: Synthesis Of the Sulfenamides Of The 14-naphthoquinonementioning

confidence: 99%