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Paper | Regular issue | Vol 38, No. 9, 1994, pp.1979-2003
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5783
Direct Polynitroaliphatic Alcohol Addition to Alkenes. 3. Synthesis, Structure and Intramolecular Electron Impact Stability of the Uniquely Structured 2,4-Dimethyl-7,7-dinitro-1,3,5-trioxacyclooctane

Raymond R. McGuire, J. Lloyd Pflug, Margaret H. Rakowsky, Scott A. Shackelford,* and Alan A. Shaffer

*Materials Chemistry Division, F.J. Seiler research Laboratory (AFMC), 2354 Vandenberg Drive, Suite 2A35, USAF Academy, Colorado 80840-6272, U.S.A.

Abstract

Mercury(I) sulfate catalyzed addition between the difunctional 2,2-dinitropropane-1,3-diol (ADIOL) and the divinyl ether (DVE) diene reactants produces either an apparent acyclic acetal oligomer, or the unexpected eight-membered 2,4-dimethyl-7,7-dinitro-1,3,5-trioxacyclooctane. Proton nmr and deuterium labeling of this heterocyclic compound reveals it is comprised of both meso and dl diastereomers caused from its two chiral carbon atoms. Because this heterocycle incorporates both gem-2,2-dinitroalkyl and cyclic trioxane acetal structural fragments into one hybrid saturated ring structure, a novel intramolecular electron impact stability comparison can be made between the structural features representative of the normally unrelated geminal polynitroalkane and cyclic polyoxane compound classes which determine the fragmentation pathway of the subject heterocycle.