Radical 1,5-Chloropentafluorosulfanylation of Unactivated Vinylcyclopropanes and Transformation into α-SF Ketones.

J Org Chem

UMR 6014 CNRS COBRA, Normandie Université, INSA Rouen, 1 rue Tesnière, Mont Saint Aignan 76821, France.

Published: October 2021

The radical 1,5-chloropentafluorosulfanylation of vinyl cyclopropanes (VCPs) initiated by EtB/O 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-SF carbonyl compounds.

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http://dx.doi.org/10.1021/acs.joc.1c01886DOI Listing

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