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Energetic Materials Trends in 5‐ and 6‐Membered Cyclic Peroxides Containing Hydroperoxy and Hydroxy Substituents
Author(s) -
Gamage NipuniDhanesha H.,
Stiasny Benedikt,
Kratz Eric G.,
Stierstorfer Jörg,
Martin Philip D.,
Cisneros G. Andrés,
Klapötke Thomas M.,
Winter Charles H.
Publication year - 2016
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201600767
Subject(s) - chemistry , hydrogen peroxide , dioxolane , solid state , peroxide , explosive material , hydrogen bond , medicinal chemistry , organic chemistry , polymer chemistry , molecule
Ten peroxide compounds based upon the 3,6‐di(hydroperoxy)‐1,2‐dioxane, 2‐hydroxy‐6‐hydroperoxy‐1,2‐dioxane, 3,5‐di(hydroperoxy)‐1,2‐dioxolane, and 3‐hydroxy‐5‐hydroperoxy‐1,2‐dioxolane skeletons have been synthesized, structurally characterized, and fully evaluated for their energetic materials properties. The solid‐state structures of these compounds are dominated by hydrogen bonding interactions involving the hydroperoxy and hydroxy groups. Energetic materials testing shows that most of the compounds are highly sensitive toward impact and friction, with similar properties to highly sensitive peroxides such as triacetone triperoxide. 3,5‐Diethyl‐5‐hydroperoxy‐1,2‐dioxolan‐3‐ol ( 3b ) and 3,5‐dimethyl‐5‐hydroperoxy‐1,2‐dioxolan‐3‐ol ( 5b ) have lower impact and friction sensitivities than the other compounds, with values that are appropriate for use as primary explosives.