TY - JOUR
T1 - Mono- and diiodo-1,2,3-triazoles and their mono nitro derivatives
AU - Chand, Deepak
AU - He, Chunlin
AU - Hooper, Joseph P.
AU - Mitchell, Lauren A.
AU - Parrish, Damon A.
AU - Shreeve, Jean'Ne M.
N1 - Publisher Copyright:
© 2016 The Royal Society of Chemistry.
PY - 2016
Y1 - 2016
N2 - 4-Iodo-1H-1,2,3-triazole (2) and 4,5-diiodo-1H-1,2,3-triazole (3) were synthesized using an efficient and viable synthetic route. The N-alkylation of 3 resulted in the formation of two tautomers. The N-alkyl-diiodo-triazoles were nitrated with 100% nitric acid to form monoiodo-mononitro-triazoles. The structures of 2-methyl-4,5-diiodo-1,2,3-triazole (5), 1-ethyl-4,5-diiodo-1,2,3-triazole (6), 1-methyl-4-nitro-5-iodo-1,2,3-triazole (8) and 1-ethyl-4-nitro-5-iodo-1,2,3-triazole (10) were confirmed by X-ray crystal analysis. All of the new triazoles were fully characterized via NMR, and infrared spectra, and elemental analyses as well as by their thermal and sensitivity properties. Decomposition products calculated using Cheetah 7 software show that these iodo-nitro triazoles liberate iodine.
AB - 4-Iodo-1H-1,2,3-triazole (2) and 4,5-diiodo-1H-1,2,3-triazole (3) were synthesized using an efficient and viable synthetic route. The N-alkylation of 3 resulted in the formation of two tautomers. The N-alkyl-diiodo-triazoles were nitrated with 100% nitric acid to form monoiodo-mononitro-triazoles. The structures of 2-methyl-4,5-diiodo-1,2,3-triazole (5), 1-ethyl-4,5-diiodo-1,2,3-triazole (6), 1-methyl-4-nitro-5-iodo-1,2,3-triazole (8) and 1-ethyl-4-nitro-5-iodo-1,2,3-triazole (10) were confirmed by X-ray crystal analysis. All of the new triazoles were fully characterized via NMR, and infrared spectra, and elemental analyses as well as by their thermal and sensitivity properties. Decomposition products calculated using Cheetah 7 software show that these iodo-nitro triazoles liberate iodine.
UR - http://www.scopus.com/inward/record.url?scp=84973649570&partnerID=8YFLogxK
U2 - 10.1039/c6dt01731b
DO - 10.1039/c6dt01731b
M3 - Article
AN - SCOPUS:84973649570
SN - 1477-9226
VL - 45
SP - 9684
EP - 9688
JO - Dalton Transactions
JF - Dalton Transactions
IS - 23
ER -