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DOI: 10.1055/s-0031-1289682
(3,3,5,5-Tetranitropiperidin-1-yl)acetic Acid: Precursor for 1,3,3,5,5-Pentanitropiperidine
Publication History
Publication Date:
30 January 2012 (online)
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Abstract
(3,3,5,5-Tetranitropiperidin-1-yl)acetic acid is a novel and economical precursor for 1,3,3,5,5-pentanitropiperidine. Treatment of 2,2-dinitropropane-1,3-diol with glycine in water at 65-70 ˚C for five hours gave (3,3,5,5-tetranitropiperidin-1-yl)acetic acid in 52% isolated yield. Nitration of the latter in a mixture of 100% nitric acid and trifluoroacetic anhydride for 12 hours gave 1,3,3,5,5-pentanitropiperidine in essentially quantitative yield. (3,3,5,5-Tetranitropiperidin-1-yl)acetic acid and 1,3,3,5,5-pentanitropiperidine were fully characterized by means of IR and NMR (¹H, ¹³C, and ¹5N) spectroscopy, differential scanning calorimetry, and elemental analysis.
Key words
cyclization - condensation - piperidines - nitration - explosives
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- Supporting Information
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