124497-50-3Relevant articles and documents
SPIROCYCLIC MEISENHEIMER COMPLEXES. XXIII. REVERSIBLE DOUBLE SMILES REARRANGEMENT IN THE 3-N-METHYL-N-PICRYLAMINO-1,2-PROPANEDIOL - 1-METHYLAMINO-2-PICRYLOXY-2-PROPANOL SYSTEM THROUGH THE INTERMEDIATE FORMATION OF TWO TAUTOMERIC MEISENHEIMER SPIRO COMPLEXES.
Knyazev, V. N.,Drozd, V. N.
, p. 1966 - 1970 (2007/10/02)
The possibility of acylotropic migration along a chain of three nucleophilic centers was established for the first time for the case of the picryl derivatives of 3-methylamino-1,2-propanediol. 3-N-methyl-N-picrylamino-1,2-propanediol is converted by the action of bases into a spirocyclic Meisenheimer complex with a five-memberd N-methyloxazolidine ring, which is present in solutions in tautomeric equilibrium with the isomeric spiro complex containing a five-membered dioxolane ring in a ratio of 10:1 (DMSO-d6).Rapid acidification of the reaction mixture leads to theformation of 1-methylamino-3-picryloxy-2-propanol hydrochloride, for which the reverse establishment of a tautomeric equilibrium between the above-mentioned spiro complexes in solutions can be observed under the influence of bases.