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

doi:10.1016/S0040-4020(01)89839-2

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

Chemistry & Biochemistry

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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 language	English (US)
Pages (from-to)	6505-6513
Number of pages	9
Journal	Tetrahedron
Volume	44
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4020(01)89839-2
State	Published - 1988

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title = "Cesium fluoroxysulfate addition to alkenes leading to vicinal fluoroalkylsulfates",

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.",

author = "Zefirov, {Nikolai S.} and Zhdankin, {Viktor V.} and Koz'min, {Anatoly S.} and Fainzilberg, {Albert A.} and Gakh, {Andrei A.} and Ugrak, {Bogdan I.} and Romaniko, {Sergei V.}",

year = "1988",

doi = "10.1016/S0040-4020(01)89839-2",

language = "English (US)",

volume = "44",

pages = "6505--6513",

journal = "Tetrahedron",

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TY - JOUR

T1 - Cesium fluoroxysulfate addition to alkenes leading to vicinal fluoroalkylsulfates

AU - Zefirov, Nikolai S.

AU - Zhdankin, Viktor V.

AU - Koz'min, Anatoly S.

AU - Fainzilberg, Albert A.

AU - Gakh, Andrei A.

AU - Ugrak, Bogdan I.

AU - Romaniko, Sergei V.

PY - 1988

Y1 - 1988

N2 - 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.

AB - 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.

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U2 - 10.1016/S0040-4020(01)89839-2

DO - 10.1016/S0040-4020(01)89839-2

M3 - Article

AN - SCOPUS:0000201277

SN - 0040-4020

VL - 44

SP - 6505

EP - 6513

JO - Tetrahedron

JF - Tetrahedron

IS - 20

ER -

Cesium fluoroxysulfate addition to alkenes leading to vicinal fluoroalkylsulfates

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