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The first thermally-induced retro-oxy-cope rearrangement

โœ Scribed by Steven W. Elmore; Leo A. Paquette


Book ID
104225399
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
192 KB
Volume
32
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The reversibility of the thermal oxy-Cope rearrangement is demonstrated with the specific example 10 t 11, and the pathway and energetics associated with this phenomenon are outlined.


๐Ÿ“œ SIMILAR VOLUMES


The aromatic oxy-Cope rearrangement
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## An aromatic oxy-Cope rearrangement can be achieved under anionic conditions (KH f HMPAl in Zow yield with a nuphthalene ring but not a phenyt. We have recently measured the activation parameters for an aromatic Cope rearrangement,l and these sug,oest that rearrangement of 4-phenyl-1-butene wou

Influence of the stereochemistry on the
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From cyclobutanones Sa-j,ten 1,2-divinylcyclobutanot la-j were prepared. A stereochemical effect was clearly evidenced : while trans 1,2-divinylcyclobutanols underwent a retro-ene ring opening, the cis isomers underwent an oxy-Cope ring enlargement. It is well known that cis 1,2-divinylcyclobutanes

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The anionic oxy-Cope rearrangement has emerged as a highly useful tool for organic synthesis. [1, 2] Various 1,5-dien-3ols readily undergo this electronic reorganization, and the usually easy preparation of the precursors contributes to the popularity of this reaction. However, a limitation of this