Radical 1,5-Chloropentafluorosulfanylation of Unactivated Vinylcyclopropanes and Transformation into α-SF5 Ketones | Zendy

FangFang Feng | Zendy; JunAn Ma | Zendy; Dominique Cahard | Zendy

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Radical 1,5-Chloropentafluorosulfanylation of Unactivated Vinylcyclopropanes and Transformation into α-SF₅ Ketones

Author(s) -

FangFang Feng,

JunAn Ma,

Dominique Cahard

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.1c01886

Subject(s) - chemistry , cyclopropane , allylic rearrangement , ozonolysis , medicinal chemistry , ring (chemistry) , transformation (genetics) , chemoselectivity , radical cyclization , ketone , stereochemistry , organic chemistry , catalysis , biochemistry , gene

The radical 1,5-chloropentafluorosulfanylation of vinyl cyclopropanes (VCPs) initiated by E 3 B/O 2 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 5 carbonyl compounds.

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