Chemistry of 1,2,4-Trioxanes: Metal-Induced Deoxygenation and Rearrangement of the 1,2,4-Trioxane Obtained by Photooxidation of β-Ionone

Mirta  Mischne

doi:10.1055/s-2002-33637

PAPER

Chemistry of 1,2,4-Trioxanes: Metal-Induced Deoxygenation and Rearrangement of the 1,2,4-Trioxane Obtained by Photooxidation of β-Ionone

Mirta Mischne*
Instituto de Química Orgánica de Síntesis (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Casilla de Correo 991, 2000 Rosario, Argentina
Fax: 54(341)4370477; e-Mail: mmischne@fbioyf.unr.edu.ar;

Abstract

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Abstract

The reactivity of 2,2,6,8-tetramethyltricyclo(6.2.2.0^1,6)dodecene (2) toward different metal salts has been explored. In the presence of Fe(II), Sn(II) and Ce(IV) ions, compound 2 underwent a rearrangement process to afford acyclic triketones Z-3 and E-3. The action of Zn powder in acetic acid resulted in an unexpected formation of furan 4 in high yield.

Key words

peroxides - trioxanes - furans - rearrangements - deoxygenation

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References

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