Synlett 2015; 26(14): 2029-2032
DOI: 10.1055/s-0034-1381042
letter
© Georg Thieme Verlag Stuttgart · New York

Pentaerythritol Trinitrate Substituted s-Tetrazine and s-Triazine

David E. Chavez*
a   Los Alamos National Laboratory, Weapons Experiments Division, Los Alamos, NM 87545, USA   Email: dechavez@lanl.gov
,
Thomas W. Myers
a   Los Alamos National Laboratory, Weapons Experiments Division, Los Alamos, NM 87545, USA   Email: dechavez@lanl.gov
,
Jacqueline M. Veauthier
a   Los Alamos National Laboratory, Weapons Experiments Division, Los Alamos, NM 87545, USA   Email: dechavez@lanl.gov
,
Margo T. Greenfield
a   Los Alamos National Laboratory, Weapons Experiments Division, Los Alamos, NM 87545, USA   Email: dechavez@lanl.gov
,
R. Jason Scharff
a   Los Alamos National Laboratory, Weapons Experiments Division, Los Alamos, NM 87545, USA   Email: dechavez@lanl.gov
,
Damon A. Parrish
b   Naval Research Laboratory, Laboratory for the Structure of Matter, Washington, DC 20375, USA
› Author Affiliations
Further Information

Publication History

Received: 13 May 2015

Accepted after revision: 28 May 2015

Publication Date:
22 July 2015 (online)


Abstract

The synthesis of pentaerythritol trinitrate persubstituted 1,2,4,5-tetrazine and 1,3,5-triazine is reported. These materials were characterized with respect to their chemical and energetic materials properties. X-ray crystallographic analyses were also performed. The UV/Vis, Raman, and cyclic voltammetry data were collected and are reported.

Supporting Information

 
  • References and Notes

  • 1 Chavez DE, Hanson SK, Veauthier JM. Angew. Chem. Int. Ed. 2013; 52: 6876
  • 5 Lange K, Koenig A, Roegler C, Seeling A, Lehmann J. Bioorg. Med. Chem. Lett. 2009; 19: 3141
  • 6 Rao BV, Dhokale S, Rajamohanan PR, Hotha S. Chem. Commun. 2013; 49: 10808
  • 7 Compound 4 – Typical Procedure PETRIN (1, 390 mg, 1.44 mmol) was placed in a 25 mL round-bottomed flask. Compound 3 (555 mg, 1.44 mmol) was then added along with CH2Cl2 (2 mL). The reaction was stirred. 4-Dimethylaminopyridine (287 mg, 2.35 mmol) was added and the reaction stirred for 2 h. The reaction was filtered through a short plug of silica, the eluent collected and evaporated to give the desired product, 4, as a reddish-pink solid (735 mg, 82%), mp 139 °C, 147 °C (dec.). 1H NMR (300 MHz, DMSO-d 6): δ = 4.68 (s, 2 H), 4.85 (s, 6 H). 13C NMR (100 MHz, DMSO-d 6): δ = 41.54, 66.83, 70.66, 165.54. IR (KBr): νmax = 3023, 2947, 2916, 1659, 1641, 1629, 1475, 1238, 1389, 1365, 1284, 1082, 1031, 1015, 993, 944, 889, 753 cm–1. Anal. Calcd for C12H16N10O20: C, 23.23; H, 2.60; N, 22.58. Found: C, 23.21; H, 2.61; N, 22.55.
  • 8 Brandt NN, Brovko OO, Chikishev AY, Paraschuk OD. Appl. Spectrosc. 2006; 60: 288
  • 10 Pop F, Riobe F, Seifert S, Cauchy T, Ding J, Dupont N, Hauser A, Koch M, Avarvari N. Inorg. Chem. 2013; 52: 5023
  • 11 Farzinnejad N, Miran Beigi AA, Fotouhi L, Torkestani K, Ghadirian HA. J. Electroanal. Chem. 2005; 580: 245
  • 12 CCDC 1053809 and CCDC 1053814 contain the supplementary crystallographic data for 4 and 6, respectively. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.