Transformation of 2-allyl-1,3-diketones to bicyclic compounds containing 1,2-dioxolane and tetrahydrofuran rings using the I 2 /H 2 O 2 system

Transformation of 2-allyl-1,3-diketones to bicyclic compounds containing 1,2-dioxolane and tetrahydrofuran rings using the I 2 /H 2 O 2 system Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2016, Volume: 57, Number: 8, Pages: 949-952 Pages count : 4 DOI: 10.1016/j.tetlet.2016.01.061

Authors

Zdvizhkov Alexander T. ¹ , Terent’ev Alexander O. ¹ , Radulov Peter S. ¹ , Novikov Roman A. ¹ , Tafeenko Viktor A. ² , Chernyshev Vladimir V. ^3,2 , Ilovaisky Alexey I. ¹ , Levitsky Dmitri O. ⁴ , Fleury Fabrice ⁴ , Nikishin Gennady I. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., 119991 Moscow, Russian Federation
2	Department of Chemistry, Moscow State University, Leninskie Gory, 119992 Moscow, Russian Federation
3	A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31 Leninsky Prosp., 119991 Moscow, Russian Federation
4	UFIP CNRS UMR 6286, Mechanism and Regulation of DNA Repair Team, Université de Nantes, 2 rue de la Houssinière, 44322, France

A one-pot procedure was developed for the assembly of bicyclic compounds containing 1,2-dioxolane and tetrahydrofuran rings based on the reaction of 2-allyl-1,3-diketones with the I2/H2O2 system. A fivefold molar excess of H2O2 and a twofold excess of I2 are required for the selective formation of tetrahydrofurodioxoles. The synthesis of these structurally complex molecules is unusual in that it does not produce the expected bridged tetraoxanes, products of the addition of several H2O2 molecules to a carbonyl group, or the products of double bond iodoperoxidation.

Zdvizhkov A.T. , Terent’ev A.O. , Radulov P.S. , Novikov R.A. , Tafeenko V.A. , Chernyshev V.V. , Ilovaisky A.I. , Levitsky D.O. , Fleury F. , Nikishin G.I.
Transformation of 2-allyl-1,3-diketones to bicyclic compounds containing 1,2-dioxolane and tetrahydrofuran rings using the I 2 /H 2 O 2 system
Tetrahedron Letters. 2016. V.57. N8. P.949-952. DOI: 10.1016/j.tetlet.2016.01.061 WOS Scopus OpenAlex

Web of science:	WOS:000370307800028
Scopus:	2-s2.0-84955457218
OpenAlex:	W2280890729

DB	Citing
OpenAlex	20
Scopus	19
Web of science	17