Cesium fluoroxysulfate addition to alkenes leading to vicinal fluoroalkylsulfates

Nikolai S. Zefirov, Viktor V. Zhdankin, Anatoly S. Koz'min, Albert A. Fainzilberg, Andrei A. Gakh, Bogdan I. Ugrak, Sergei V. Romaniko

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

The addition of cesium fluoroxysulfate (1) to a variety of alkenes (1-hexene, styrene, E-stilbene, cyclohexene, diene 14) proceeds under mild conditions giving the previously unknown vicinal fluoro alkyl sulfates. The structures of these products were rigorously established by thorough 1H, 19F and 13C NMR data analyses. The studied reactions exhibit low regio- and stereo- selectivities with a preference for anti-Markovnikov- and syn-addition. The predominance of cis-product formation is consistent with a concerted mechanism for the addition.

Original languageEnglish (US)
Pages (from-to)6505-6513
Number of pages9
JournalTetrahedron
Volume44
Issue number20
DOIs
StatePublished - 1988

Fingerprint Dive into the research topics of 'Cesium fluoroxysulfate addition to alkenes leading to vicinal fluoroalkylsulfates'. Together they form a unique fingerprint.

  • Cite this

    Zefirov, N. S., Zhdankin, V. V., Koz'min, A. S., Fainzilberg, A. A., Gakh, A. A., Ugrak, B. I., & Romaniko, S. V. (1988). Cesium fluoroxysulfate addition to alkenes leading to vicinal fluoroalkylsulfates. Tetrahedron, 44(20), 6505-6513. https://doi.org/10.1016/S0040-4020(01)89839-2