Boron Trifluoride as an Efficient Catalyst for the Selective Synthesis of Tricyclic Monoperoxides from β,δ-Triketones and H2O2

Alexander O. Terent’ev; Ivan A. Yaremenko; Vera A. Vil’; Valery M. Dembitsky; Gennady I. Nikishin

doi:10.1055/s-0032-1317895

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(2): 246-250
DOI: 10.1055/s-0032-1317895

paper

Boron Trifluoride as an Efficient Catalyst for the Selective Synthesis of Tricyclic Monoperoxides from β,δ-Triketones and H₂O₂

Alexander O. Terent’ev*

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation Fax: +7(499)1355328 eMail: terentev@ioc.ac.ru

,

Ivan A. Yaremenko

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation Fax: +7(499)1355328 eMail: terentev@ioc.ac.ru

,

Vera A. Vil’

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation Fax: +7(499)1355328 eMail: terentev@ioc.ac.ru

,

Valery M. Dembitsky

^bInstitute for Drug Research, P. O. Box 12065, Hebrew University, Jerusalem 91120, Israel

,

Gennady I. Nikishin

^aN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation Fax: +7(499)1355328 eMail: terentev@ioc.ac.ru

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Abstract

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Abstract

Boron trifluoride was found to serve as an efficient catalyst for the reaction of β,δ-triketones with H₂O₂producing tricyclic monoperoxides in yields from 48–93%. BF₃ acts simultaneously as a catalyst and co-solvent. The synthesis can be scaled up to tens of grams. The resulting peroxides can be easily isolated from the reaction mixture by column chromatography.

Key words

boron trifluoride - catalyst - peroxides - triketones - hydrogen peroxide

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Referenzen

References

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