Dialkoxy disulfide

Since dialkylperoxides are dangerous to handle, only three different ROCgo radicals have prepared by reaction with these reagents (Scheme 6.4). Dialkoxy-disulfides can easily be synthesized with any kind of R and are, therefore, a more convenient source of RO radicals [36]. 

Dithiabicyclo[3.1.1]heptane-2-one 6-oxide derivatives 29 along with two regioisomeric products 30 and 31 were obtained in multiple rearrangements of propargylic dialkoxy disulfides <2003JA14290, 2003TL777>. 

It was reported that cyclic dialkoxy disulfides 171 undergo ring contraction to a thionosulfite 172 followed by extrusion of sulfur to give the sulfoxylate 173 and the mechanism of these transformations discussed <07JOC3906>. 

Scheme 39 Mixed allylic sulfinates by alcoholysis of dialkoxy disulfides...

Scheme 36 [2,3]Sigmatropic rearrangement of bis-propargylic dialkoxy disulfides...

S, S-Dialkoxy disulfides Iliiolsulfonic acid esters - acids Thiolsultones... 

Novel example of this reaction type are given by the copper-catalyzed decomposition of ethyl diazoacetate in the presence of bis(dialkoxyphosphoryl)disulfides 374 350 where P/S insertion sometimes accompanies the S/S insertion, and of bis(dialkoxy-thiophosphoryl)trisulfides 375 351 where desulfurization to give the disulfide derived product occurs during the reaction. Only P/S insertion product was obtained from bis(dialkoxyphosphoryl)trisulfide or -tetrasulfide 376 the copper-catalyst is dispensable in this case351K... 

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