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The acid-catalyzed Wagner-Meerwein rearrangement of dieldrin

✍ Scribed by John W. ApSimon; John A. Buccini; Alfred S.Y. Chau


Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
163 KB
Volume
15
Category
Article
ISSN
0040-4039

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✦ Synopsis


In acidic media, aldrin' and its dechloro-derivatives 3 undergo Wagner-Meerwein type rearrangements to form derivatives of isodrin: an analogous rearrangement of dieldrin has not yet been reported.

Reaction of dieldrin

with various acids is reported to give either 4-oxo-4,5-dihydroaldrin 485

or the normal trans products resulting from opening of the epoxide ring 6 .

This letter reports a Wagner-Meerwein type skeletal rearrangement of dieldrin in either acetic anhydride/sulfuric acid or boron trifluoride/methanol mixtures to give compounds of general formula VII as the major products.

A mixture of purified dieldrin and acetic anhydride/sulfuric acid (100/l) was refluxed for one hour to yield, after isolation', three pure crystalline


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