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

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 deuter...

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Bibliographic Details
Published inHeterocycles Vol. 38; no. 9; pp. 1979 - 2003
Main Authors MCGUIRE, RR, PFLUG, JL, RAKOWSKY, MH, SHACKELFORD, SA, SHAFFER, AA
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.09.1994
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ETHERS
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Summary: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.
ISSN:0385-5414
DOI:10.3987/com-91-5783