Six Peroxide Groups in One Molecule - Synthesis of Nine-Membered Bicyclic Silyl Peroxides

Compounds containing two nine‐membered peroxide rings bridged by an ethane, ethene, or ethyne group were synthesized by the reactions of 1,2‐bis[dichloro(alkyl)silyl]ethanes, (E)‐1,2‐bis[dichloro(methyl)silyl]ethene, or 1,2‐bis[dichloro(methyl)silyl]ethyne with 1,1′‐dihydroperoxydicycloalkyl peroxid...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-11, Vol.2014 (31), p.6877-6883
Main Authors: Arzumanyan, Ashot V., Terent'ev, Alexander O., Novikov, Roman A., Lakhtin, Valentin G., Chernyshev, Vladimir V., Fitch, Andrew N., Nikishin, Gennady I.
Format: Article
Language:English
Subjects:
Chlorine
Cyclization
Energetic materials
Peroxides
Silanes
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Summary:Compounds containing two nine‐membered peroxide rings bridged by an ethane, ethene, or ethyne group were synthesized by the reactions of 1,2‐bis[dichloro(alkyl)silyl]ethanes, (E)‐1,2‐bis[dichloro(methyl)silyl]ethene, or 1,2‐bis[dichloro(methyl)silyl]ethyne with 1,1′‐dihydroperoxydicycloalkyl peroxides. Each ring is formed by the replacement of two geminal chlorine atoms at the silicon atom with the hydroperoxide groups of one peroxide molecule. The cyclization is regioselective. The possible 12‐membered bicyclic peroxide products are not produced. Unexpectedly, the peroxides are extremely explosive. The reactions of 1,2‐bis[dichloro(alkyl)silyl]ethanes with 1,1‐dihydroperoxy‐tert‐butylcyclohexane give only bicyclic peroxides containing two six‐membered rings also through the replacement of two geminal chlorine atoms at the silicon atom by the hydroperoxide groups of one dihydroperoxide molecule. Compounds containing two nine‐membered peroxide rings bridged by an ethane, ethene, or ethyne group are synthesized. Each ring is formed by the replacement of two geminal chlorine atoms at the silicon atom with the hydroperoxide groups of one peroxide molecule. The peroxides are isolated by crystallization or silica gel filtration; unexpectedly, all of these compounds are extremely explosive.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201402895