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 |
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| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | 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. |
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| ISSN: | 0018-019X 1522-2675 |
| DOI: | 10.1002/hlca.19770600232 |