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

✍ Scribed by Manfred Schlosser; Yvonne Bessière


Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
461 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis


Abstract

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.