Degenerate rearrangement of long-lived 9-cyclopropyl-9,10-dimethyl-9,10-dihydrophenanthren-9-ylium: Migration of cyclopropyl group

Dynamic NMR study showed that long-lived 9-cyclopropyl-9,10-dimethyl-9,10-dihydrophenanthren-9-yl cation generated from 9-cyclopropyl-9,10-dimethyl-9,10-dihydrophenanthren-9-ol in HSO₃F-SO₂ClF-CD₂Cl₂ at −100 to −75°C undergoes fast degenerate 1,2-shift of the cyclopropyl group. The Arrhenius paramet...

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Bibliographic Details
Published inRussian journal of organic chemistry Vol. 46; no. 3; pp. 311 - 317
Main Authors Genaev, A. M, Sal'nikov, G. E, Shubin, V. G
Format Journal Article
LanguageEnglish
Published Dordrecht Dordrecht : SP MAIK Nauka/Interperiodica 01.03.2010
SP MAIK Nauka/Interperiodica
Springer Nature
Subjects
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Organic Chemistry
Physical Sciences
Science & Technology
Fluorosulfonic Acid
Colorless Oily Substance
Electrophilic Substitution Reaction
Cyclopropane Ring
Cyclopropyl Group
PHENANTHRENONIUM IONS
ARYL GROUPS
ABILITY
MODEL
CARBONIUM-IONS
1,2-SHIFT
CATIONS
ATOM
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Summary:Dynamic NMR study showed that long-lived 9-cyclopropyl-9,10-dimethyl-9,10-dihydrophenanthren-9-yl cation generated from 9-cyclopropyl-9,10-dimethyl-9,10-dihydrophenanthren-9-ol in HSO₃F-SO₂ClF-CD₂Cl₂ at −100 to −75°C undergoes fast degenerate 1,2-shift of the cyclopropyl group. The Arrhenius parameters for this process were determined: E a = 33.7 kJ/mol, log A = 13.0.
Bibliography:http://dx.doi.org/10.1134/S1070428010030012
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428010030012