Über die Einwirkung von Schwefel auf Diazoalkane

Abstract

Die Einwirkung von elementarem Schwefel auf Diaryldiazomethane liefert Tetraayläthylensulfide in guter Ausbeute, Diarylthioketone sind als Zwischenprodukte anzunehmen.

Selenobenzophenones and Diazoalkanes: Isolation of Tetraarylethylenes by the Reaction of Benzophenone Hydrazones with Diselenium Dibromide

“…As previously stated, we have shown that the reaction of the selenobenzophenones 1 with diaryldiazomethanes 2 gave tetraarylethylenes 5 in good yields. The reported methods for the formation of tetraarylethylenes 5 include thermolysis of diaryl thioketones,13 decomposition of diaryldiazomethanes by HClO 4 ,14 reduction of tetraarylethylene sulfides,15 reaction of diaryldiazomethanes with o ‐sulfobenzoic anhydride,16 reaction of diaryl thioketones with Cu,17 and ytterbium metal‐mediated desulfurization and coupling reaction of diaryl thioketones 18. However, these methods require isolation of diaryl thioketones or diaryldiazomethanes.…”

Reactions of sterically congested 1,6‐ and 1,7‐bis(diazo)alkanes with elemental sulfur and selenium: Formation of cyclohexene, 1,2‐dithiocane, 1,2‐diselenocane, and 1,2,3‐triselenecane derivatives

“…Since it has been reported that the reaction of diazoalkanes and elemental selenium provided selenoketones [2,4], the intermediate diazoselenoketone 4 is expected to form by the reaction of 5 with elemental selenium. It was also reported that the reactions of diazoalkanes with elemental sulfur are synthetically useful to prepare alkenes or episulfides [5][6][7]. We report here the formation of 1 by the reaction of 5 with elemental selenium in good yield and the formation of rare classes of sulfur-and selenium-containing heterocycles.…”

Reactions Involving Hetero Atoms

“…Table IV records the product ratios of [89] and [90] in allylic sulfide-dichlorocarbene reactions. The reaction of diazoalkanes with thiophosgene and with thioketones was reported by Staudinger and Siegwart (205) nearly 40 years ago; e.g., diphenyldiazomethane with thiophosgene gave 2,2-dichloro-3,3-diphenylthiirane [91] action of diazoalkanes with sulfur also afforded thiiranes (210,211). In all of these reactions, however, it is not clear whether the diazoalkane or the carbene derived from it is the reacting species.…”