Radical 1,5-Chloropentafluorosulfanylation of Unactivated Vinylcyclopropanes and Transformation into α-SF 5 Ketones - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2021

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

Résumé

The radical 1,5-chloropentafluorosulfanylation of vinyl cyclopropanes (VCPs) initiated by Et 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. Scheme 2. Scope I of the Pentafluorosulfanylation of VCPs: Vinyl Substituent Effect a,b a See Experimental Section for detailed procedures. b Z/E ratios were determined on crude reaction mixtures. c Two equivalents of SF 5 Cl were required to reach full conversion.

Domaines

Chimie organique
Fichier principal
Vignette du fichier
J Org Chem D Cahard 1 9 2021.pdf (737 Ko) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-03357178 , version 1 (30-09-2021)

Identifiants

Citer

Fang-Fang Feng, Jun-An Ma, Dominique Cahard. Radical 1,5-Chloropentafluorosulfanylation of Unactivated Vinylcyclopropanes and Transformation into α-SF 5 Ketones. Journal of Organic Chemistry, In press, ⟨10.1021/acs.joc.1c01886⟩. ⟨hal-03357178⟩
15 Consultations
98 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More