66909-11-3Relevant articles and documents
The Stabilities of Meisenheimer Complexes. Part 27. The Effects of Gem-Dimethyl Substitution and Ring-Size on Spiro-Complex Formation.
Crampton, Michael R.,Routledge, Paul J.,Wilson, Penelope M.
, p. 1972 - 1993 (2007/10/02)
In the presence of aqueous sodium hydroxide, 1-(2,2-dimethyl-3-hydroxypropoxy)-2,4,6-trinitrobenzene and -2,4-dinitronaphthalene cyclise to give spiro-adducts.Comparison with the corresponding 3-hydroxypropyl ethers shows that, unusually, the gem-dimethyl substituents do not have a large effect on rate and equilibrium constants for cyclisation.The ? adduct initially formed from 1-(6-hydroxyhexoxy)-2,4,6-trinitrobenzene results from hydroxide attack at the 3-position rather than cyclisation, while 1-(6-hydroxyhexoxy)-2,4-dinitronaphthalene hydrolyses without formation of an observable intermediate.The rate coefficients for hydroxide attack at the 1-position of the substrate, giving picric acid or 2,4-dinitronaphthol, have been measured.
