Synthesis of 1,3,5,5–tetranitrohexahydropyrimidine–2,2,4,4,6,6–d6 (DNNC–d6) and its adiol–d4 precursor using paraformaldehyde–d2 and unlabeled reaction ingredients

✍ Scribed by Scott A. Shackelford

• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: French
• Weight: 476 KB
• Volume: 29
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580291104

✦ Synopsis

Abstract

Using commercially available paraformaldehyde–d~2~, the subject compounds were synthesized with unlabeled reactants and ordinary solvents. The 2,2–dinitropropane–1,3‐diol–1,1,3,3–d~4~ (ADIOL–d~4~) precursor was produced in greater than 99% isotopic purity with aqueous depolymerized paraformaldehyde–d~2~ and CH~3~NO~2~ in alkaline solution followed by oxidative AgNO~3~/NaNO~2~ nitration; then, ADIOL–d~4~ and depolymerized paraformaldehyde–d~2~ with t‐butylamine in methanol afforded cyclic 1,3–di–t‐butyl–5,5–dinitrohexahydropyrimidine–2,2,4,4,6,6–d~δ~ (DBNP–d~6~). The 97% isotopically pure DNNC–d~6~ product resulted in 71% yield from an anhydrous HNO~3~ nitration of DBNP–d~6~.