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Selenium Dibromide as a Reagent for Selective Allylic Bromination of Diacetylbetulin and Lupeol

I. V. Bodrikov,Yu. A. Kurskii,A. A. Chiyanov,A. Yu. Subbotin

Russian Journal of Organic Chemistry（2022）

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Abstract
Selenium dibromide selectively brominates lupeol or diacetylbetulin in the presence of NaHCO 3 to form an allylic isomer solely. In the absence of soda, the released HBr catalyzes the rearrangement of the allylic isomer into vinylic isomers.
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Key words
selenium dibromide,lupeol,diacetylbetulin,electrophilic substitution,bromination,regioselectivity
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