Structurally Biased 2-Fluoroallyl Cations as Generated - or not Generated - in Cyclopropane Ring-opening Reactions

Structurally Biased 2-Fluoroallyl Cations as Generated - or not Generated - in Cyclopropane Ring-opening Reactions

The silver ion‐catalysed ring‐opening of 2‐t‐butyl‐1‐chloro‐1‐fluoro‐2‐methyl‐cyclopropane (see Scheme 2) gave the expected mixture of primary and tertiary fluoroalkenols, whereas a tricyclic analog (bornane‐spiro‐chlorofluorocyclopropane) (see Scheme 3) exclusively underwent a Wagner/Meerwein rearr...

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Veröffentlicht in:Helvetica chimica acta 1977-03, Vol.60 (2), p.590-597
Hauptverfasser: Schlosser, Manfred, Bessière, Yvonne
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container_title Helvetica chimica acta
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creator Schlosser, Manfred
Bessière, Yvonne
description The silver ion‐catalysed ring‐opening of 2‐t‐butyl‐1‐chloro‐1‐fluoro‐2‐methyl‐cyclopropane (see Scheme 2) gave the expected mixture of primary and tertiary fluoroalkenols, whereas a tricyclic analog (bornane‐spiro‐chlorofluorocyclopropane) (see Scheme 3) exclusively underwent a Wagner/Meerwein rearrangement upon ionization to lose finally a proton affording a 2‐fluoro‐1,4‐diene.
doi_str_mv 10.1002/hlca.19770600232
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title Structurally Biased 2-Fluoroallyl Cations as Generated - or not Generated - in Cyclopropane Ring-opening Reactions
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