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The rearrangement of tertiary alicyclic hydroperoxides in acid

โœ Scribed by Ronald D. Bushick


Publisher
Elsevier Science
Year
1971
Tongue
French
Weight
199 KB
Volume
12
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The recent paper by Deno and co-workers' has p-ted us to report the results obtaimd some time ago in our laboratory regarding the rearr vt of tertiary alicyclic hydroperoxides. Rearrangements of aliphatic alkyl hydroperoxides have not been explored in luch depth.

Perhaps the most well-known example of such a rearrent is exemplified by the studies of Hoffman and Board.' Diisobutylene in the presence of hydrogen peroxide and 25% sulfuric acid formed 2,4,4-ttimethyl-2-pentyl hydroperoxide which uaderwent cleavage in 70% sulfuric acid to


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Lithium aluminium hydride reduction of artemisinin produces two unexpected rearrangement products in addition to those reported previously. The structure of the major rearrangement product, a tertiary hydroperoxide, was determined by 2D-NMR and chemical reactions. A mechanism is proposed for this re