Issue 10, 1987
From the journal:

Journal of the Chemical Society, Chemical Communications

Electrophile-induced rearrangement of 1,2,4-trioxanes. Formation of 1-benzofuran and 2H-1-benzopyrans

Charles W. Jefford,   Jean-Claude Rossier  and  John Boukouvalas  

Abstract

3,3,6,10b-Tetramethyl-4a, 10b-dihydronaphtho[2,1-e][1,2,4]trioxane and its 3,3-spirocyclic cyclopentane analogue on treatment with an excess of trimethylsilyl trifuloromethanesulphonate for 10 min at 24 °C rearrange to give 2-(2-oxopropyl)-3-methyl-1-benzofuran in high yield; in similar fashion the 3-methyl, n-butyl, and phenyl derivatives of 3,10b-epidioxy-2,3,4a,10b-tetrahydro-6-methyl-1H-naphtho[2,1-b]pyran give the 3-oxobutyl,3-oxoheptyl, and 3-phenyl-3-oxopropyl derivatives of 2-formyl-3-methyl(2H)-1-benzopyran.

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Article information

DOI
https://doi.org/10.1039/C39870000713
Article type
Paper

J. Chem. Soc., Chem. Commun., 1987, 713-714

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Electrophile-induced rearrangement of 1,2,4-trioxanes. Formation of 1-benzofuran and 2H-1-benzopyrans

C. W. Jefford, J. Rossier and J. Boukouvalas, J. Chem. Soc., Chem. Commun., 1987, 713 DOI: 10.1039/C39870000713

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