ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19860690735
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