[Hydroxy(tosyloxy)iodo]benzene: A Tosyloxylating Agent with Selectivity for Ketones in the Reactions with Benzalacetones

Prakash, Om; Sharma, Nitya; Ranjan, Pooja

doi:10.1080/00397910903321090

Cited by 5 publications

(1 citation statement)

References 22 publications

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“…With methyl styryl ketone, α-mesyloxylated product 29 was exclusive. 27,28 With certain substrates, we observed a profound effect on product selectivity and distribution when the I(III) oxidant and/or sulfonic acid was varied (Scheme 5). For example, when N-(3-buten-1-yl)phthalimide was stirred with PhI(OPiv)2 and MsOH in CH2Cl2, the major product was the expected dimesyloxylated compound 30 accompanied by a minor amount of mesyloxy-hydroxy compound 31 (Scheme 5).…”

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confidence: 98%

A Study of Alkene Disulfonoxylation

Sathyamoorthi,

Kelley

2024

Preprint

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We have developed convenient protocols for alkene disulfonoxylation, which involve stirring alkene substrate with a commercial I(III) oxidant and sulfonic acid in CH2Cl2 at ambient temperature. The reactions can be performed open to air without any special precautions to exclude moisture and, in most cases, deliver the products of vicinal disulfonoxylation. Where relevant, the reactions are stereospecific and furnish the products of syn-disulfonoxylation. Our protocols work best with terminal alkene substrates, but other substitution patterns are also compatible. With alkene substrates bearing appropriately positioned esters, sulfonoxylated lactones are the major products. With certain styrenyl alkenes, the products of geminal disulfonoxylation are exclusive. For this last reaction type, our results suggest that literature reports of related transformations contain misassigned product structures.

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confidence: 98%