53004-18-5Relevant academic research and scientific papers
SPIROCYCLIC MEISENHEIMER COMPLEXES XVI. EFFECT OF THE NITRO GROUP AS A SUBSTITUENT IN THE PYROCATECHOL UNIT ON THE CYCLIZATION OF POLYNITROPHENYL ETHERS OF PYROCATECHOL TO DIPHENYLENE DIOXIDES
Knyazev, V. N.,Drozd, V. N.,Mozhaeva, T. Ya.
, p. 1471 - 1477 (2007/10/02)
As a result of the reversible Smiles rearrangement the intramolecular cyclization of 2-picryloxy-4-nitrophenol leads to the formation of two regioisomeric 1,3,7- and 1,3,8-trinitrodiphenylene dioxides in a ratio of 1 : 2, whereas only one unrearranged 1,3,6-trinitrodiphenylene dioxide is formed from 2-picryloxy-6-nitrophenol.The cyclization of 2-(2,4-dinitrophenoxy)-4-nitrophenol takes place with significantly greater difficulty and leads to the rearranged 2,8-dinitrodiphenylene dioxide.Trinitrocyclohexadienide spiro complexes with 4-nitro-, 5-nitro-, and 5,6-dichlorobenzodioxolane rings were fixed and isolated in the form of triethylammonium salts.
