Radical 1,5-Chloropentafluorosulfanylation of Unactivated Vinylcyclopropanes and Transformation into α-SF<sub>5</sub> Ketones
Fangfang Feng, Jun‐An Ma, Dominique Cahard
Abstract
The radical 1,5-chloropentafluorosulfanylation of vinyl cyclopropanes (VCPs) initiated by Et3B/O2 affords allylic pentafluorosulfanyl/homoallylic chloride products through the ring-strain release of the cyclopropane. The VCP substitution pattern was investigated. The utility of this reaction was illustrated in post-transformation of the C═C bond by ozonolysis, giving access to valuable α-SF5 carbonyl compounds.
Topics & Concepts
ChemistryCyclopropaneAllylic rearrangementOzonolysisMedicinal chemistryRing (chemistry)Transformation (genetics)ChemoselectivityRadical cyclizationKetoneStereochemistryOrganic chemistryCatalysisBiochemistryGeneCyclopropane Reaction MechanismsFluorine in Organic ChemistrySulfur-Based Synthesis Techniques