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An unusual effect of selenium substituents on the regiochemistry of a baeyer-villiger rearrangement

✍ Scribed by Barry M. Trost; Peter Buhlmayer; Michael Mao

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
201 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

The regioselectivity of a Baeyer-Villiger oxidation of a cyclobutanone is dependent upon the oxidation state of a proximal selenium substituent. for the selenium dioxide-hydrogen peroxide oxidation of ketones. Sharpless, K. B. ; Gordon, K.M. J. Am. Chem. Soq . 1976, 98, 300. 9. It can be argued that perbenzeneseleninic acid is responsible for the Baeyer-Villiger reaction in one case and not the other. However, such a suggestion does not account for why a change in regiochemistry would be expected.

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## Abstract The acid catalyzed rearrangement of 1‐bromotetracyclo[4.3.0.0^2.5^0^3.8^]nonan‐4‐one 1b has been studied. With aqueous HBr, the exclusive formation of 2,7‐dibromotricyclo[4.2.1.0^3.7^]‐nonan‐4‐one **4b** was observed. This structure was established by X‐ray analysis. The divergency in b