New Preparation of 1,2,4,5,7,8-Hexaoxonanes

Alexander O. Terent'ev ,*^† Maxim M. Platonov ,^† Eduard J. Sonneveld ,^‡ Rene Peschar ,^‡ Vladimir V. Chernyshev ,^§^‖ Zoya A. Starikova ,^⊥ and Gennady I. Nikishin ^†

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation, Laboratory for Crystallography, Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Valckenierstrasse 65, Amsterdam 1018 XE, The Netherlands, Department of Chemistry, Moscow State University, 119992 Moscow, Russian Federation, A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, 31 Leninsky prosp., 119991 Moscow, Russian Federation, and A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation

J. Org. Chem., 2007, 72 (19), pp 7237–7243

DOI: 10.1021/jo071072c

Publication Date (Web): August 22, 2007

Abstract

A new versatile procedure was developed for the synthesis of 1,2,4,5,7,8-hexaoxonanes based on the Lewis acid catalyzed reaction of acetals with 1,1‘-dihydroperoxydicycloalkyl peroxides. The procedure substantially extends the structural diversity of these compounds and, in most cases, allows the synthesis of these compounds in higher yields (to 96%) and with higher selectivity. Complexation of hexaoxonane with chloroform was documented for the first time. The structures of several triperoxides were established by X-ray diffraction.

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New Preparation of 1,2,4,5,7,8-Hexaoxonanes

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New Preparation of 1,2,4,5,7,8-Hexaoxonanes

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