Phosphomolybdic and phosphotungstic acids as efficient catalysts for the synthesis of bridged 1,2,4,5-tetraoxanes from β-diketones and hydrogen peroxide

Phosphomolybdic and phosphotungstic acids as efficient catalysts for the synthesis of bridged 1,2,4,5-tetraoxanes from β-diketones and hydrogen peroxide Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2013, Volume: 11, Number: 16, Article number : 2613, Pages count : DOI: 10.1039/c3ob27239g

Authors

Terent'ev Alexander O. ¹ , Yaremenko Ivan A. ¹ , Vil' Vera A. ¹ , Moiseev Igor K. ² , Kon'kov Sergey A. ² , Dembitsky Valery M. ³ , Levitsky Dmitri O. ⁴ , Nikishin Gennady I. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Leninsky Prospect 47, Moscow, Russian Federation
2	Samara State Technical University, Molodogvardeyskaya Str. 244, 443100 Samara, Russian Federation
3	Institute for Drug Research, P.O. Box 12065, Jerusalem 91120, Israel
4	Université de Nantes, 44322 Nantes Cedex 03, France

Phosphomolybdic acid (PMA) and phosphotungstic acid (PTA) efficiently catalyze the addition of H2O2 to β-diketones to form bridged 1,2,4,5-tetraoxanes. These reactions are not accompanied by the formation of monocyclic peroxides containing hydroxy and hydroperoxide groups or polymeric peroxides. The use of these catalysts made it possible to obtain bridged tetraoxanes from easily oxidizable benzoylacetone derivatives and α-unsubstituted β-diketones. The syntheses are scaled up to ten grams. The resulting peroxides can be easily isolated from the reaction mixture by column chromatography. The yield of tetraoxanes depends on the structure of β-diketone and varies from 12 to 83%. NMR monitoring of two bridged 1,2,4,5-tetraoxanes synthesis was carried out.

Terent'ev A.O. , Yaremenko I.A. , Vil' V.A. , Moiseev I.K. , Kon'kov S.A. , Dembitsky V.M. , Levitsky D.O. , Nikishin G.I.
Phosphomolybdic and phosphotungstic acids as efficient catalysts for the synthesis of bridged 1,2,4,5-tetraoxanes from β-diketones and hydrogen peroxide
Organic & Biomolecular Chemistry. 2013. V.11. N16. 2613 . DOI: 10.1039/c3ob27239g WOS Scopus OpenAlex

≡ Web of science:	WOS:000316803900010
≡ Scopus:	2-s2.0-84876982098
≡ OpenAlex:	W2036118188