Synthesis of 1-hydroperoxy-1′-alkoxyperoxides by the iodine-catalyzed reactions of geminal bishydroperoxides with acetals or enol ethers

Synthesis of 1-hydroperoxy-1′-alkoxyperoxides by the iodine-catalyzed reactions of geminal bishydroperoxides with acetals or enol ethers Full article

Journal

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

Output data

Year: 2008, Volume: 6, Number: 23, Article number : 4435, Pages count : DOI: 10.1039/b809661a

Authors

Terent'ev Alexander O. ¹ , Platonov Maxim M. ¹ , Krylov Igor B. ¹ , Chernyshev Vladimir V. ^2,3 , Nikishin Gennady I. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow, Russian Federation
2	A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Leninsky prospect 31, Moscow, Russian Federation
3	Department of Chemistry, Moscow State University, Moscow, Russian Federation

It was found that iodine-catalyzed reactions of geminal bishydroperoxides with acetals proceed with the replacement of only one alkoxy group by the peroxide group to give previously unknown structures of 1-hydroperoxy-1′-alkoxyperoxides in yields up to 64%. The same compounds are formed in the iodine-catalyzed reactions of geminal bishydroperoxides with enol ethers. The nature of the solvent has a decisive influence on the formation of 1-hydroperoxy-1′-alkoxyperoxides. In the series of Et2O, THF, EtOH, CHCl3, CH3CN, and hexane, the best results were obtained with the use of Et2O or THF as the solvent.

Terent'ev A.O. , Platonov M.M. , Krylov I.B. , Chernyshev V.V. , Nikishin G.I.
Synthesis of 1-hydroperoxy-1′-alkoxyperoxides by the iodine-catalyzed reactions of geminal bishydroperoxides with acetals or enol ethers
Organic & Biomolecular Chemistry. 2008. V.6. N23. 4435 . DOI: 10.1039/b809661a WOS Scopus OpenAlex

≡ Web of science:	WOS:000261744800021
≡ Scopus:	2-s2.0-56349153148
≡ OpenAlex:	W2001202673