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Synthesis 2012(5): 731-734  
DOI: 10.1055/s-0031-1289682
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

(3,3,5,5-Tetranitropiperidin-1-yl)acetic Acid: Precursor for 1,3,3,5,5-Pentanitropiperidine

Rajendra P. Singh, Jean’ne M. Shreeve*
Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA
Fax: +1(208)8859165; e-Mail: jshreeve@uidaho.edu;
Further Information

Publication History

Received 18 November 2011
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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