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Scientific article
English

The Formation of Bridged Bicyclic 1,2,4-Trioxanes by Intramolecular Capture of β-Hydroperoxy Cations

Published inHelvetica chimica acta, vol. 69, no. 7, p. 1778-1786
Publication date1986-10-29
Abstract

The 1,4-endoperoxide, prepared from 3-(4-methylnaphth-1-yl)propanal by photo-oxygenation in CH2Cl2, gave on treatment with Amberlyst-15®, 3,10b-epidioxy-2,3,4a,10b-tetrahydro-6-methyl-1H-naphtho[2,1-b] pyran in 85% yield. Its structure was determined by X-ray crystal structure analysis. The 1,2,4-trioxane moiety is locked in a twist-boat conformation with trans fusion to the parent six-membered ring. The 1,4-endoperoxides of the methyl, butyl, and phenyl ketone analogues of the aforementioned aldehyde underwent similar acid-catalyzed rearrangement to the corresponding bridged bicyclic trioxanes in 94, 47, and 48% yields, respectively.

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Citation (ISO format)
JEFFORD, Charles et al. The Formation of Bridged Bicyclic 1,2,4-Trioxanes by Intramolecular Capture of <i>β</i>-Hydroperoxy Cations. In: Helvetica chimica acta, 1986, vol. 69, n° 7, p. 1778–1786. doi: 10.1002/hlca.19860690735
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ISSN of the journal0018-019X
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