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
📜 SIMILAR VOLUMES
Mechanism of Wagner-Meerweln rearrangement 11 , especially the rearrangement of P-phenylethyl cation and norbonyl cation system, has been vastly studied on
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