120695-70-7Relevant academic research and scientific papers
Synthesis and structural characterization of lithium, sodium and potassium complexes supported by a tridentate amino-bisphenolate ligand
Durango-García, Clara J.,Rufino-Felipe, Ernesto,López-Cardoso, Marcela,Mu?oz-Hernández, Miguel-ángel,Montiel-Palma, Virginia
, p. 248 - 258 (2018)
Reactions of methylamino-N,N-bis(2-methylene-4,6-di-tert-butylphenol) (1) with one or two equivalents of bulk Li, Na or K metals in THF or DMSO render mono or dialkali metal complexes depending on the stoichiometric ratio of the reactants. The metal-methylamino-N-(2-methylene-4,6-tert-butylphenol)–N-(2-methylene-4,6-tert-butylphenolate) complexes, 2Li, 2Na and 2K, are generated upon the substitution of a single phenol hydrogen of 1. In the solid state, complex 2Na is a dimer due to the establishment of two symmetric hydrogen bonds between two adjacent molecules. The Na center also engages into the formation of a ten-membered metallacycle ring with a butterfly-like structure. Due to dimerization, an intermolecular six-membered core is formed involving two sodium and four oxygen atoms. The weakly coordinated nitrogen atom from the ligand is nearly perpendicular to the hexagonal core. The dimetal-methylamino-N,N′-bis(2-methylene-4,6-di-tert-butylphenolate) complexes, 3Li, 3Na and 3K result from metal substitution of the two phenol hydrogens from ligand 1. The SC-XRD structures of 3Li and 3Na are discreet, each incorporating two metal atoms in different coordination environments. Ten-membered rings with boat-boat conformations are also observed as are rhombic central M2O2 cores. The molecular structure of 3K in DMSO shows a higher degree of aggregation. It effectively comprises four K atoms, two ligand backbones and seven solvent molecules forming a central four-membered K2O2 ring perpendicular to an eight-membered structure formed also by K and O atoms spanning over the two ligand moieties.
New opportunities for duff reaction
Belostotskaya,Komissarova,Prokof'Eva,Kurkovskaya,Vol'Eva
, p. 703 - 706 (2007/10/03)
Reaction of 2,4-di-tert-butylphenol with urotropin in conditions of Duff reaction takes an abnormal route and instead of the expected di-tert-butylsalicylaldehyde provides a mixture of N-substituted 3,5-di-tert-butyl-2-hydroxybenzylamines and redox conjugate benzoxazines containing mostly 6,8-di-tert-butyl-3-(3,5-di-tert-butyl-2-hydroxybenzyl)-2H-3, 4-dihydrobenz[e][1,3]oxazine. A solvolysis of an individual benzoxazine in the system HO(CH2)2OH-H2O-HCl affords di(3,5-di-tert-butyl-2-hydroxybenzyl)amine, and in AcOH 3,5-di-tert- butylsalicilaldehyde. A mechanism of Duff reaction was suggested involving the formation of a benzoxazine intermediate. 2005 Pleiades Publishing, Inc.
REACTION OF 2,4-DI-TERT-BUTYLPHENOL WITH FORMYLATING AGENTS
Komissarova, N. L.,Belostotskaya, I. S.,Shubina, O. V.,Grishina, E. A.,Ershov, V. V.
, p. 157 - 159 (2007/10/02)
Formylation of 2,4-di-tert-butylphenol leads to other products rather than the expected 3,5-di-tert-butylsalicylaldehyde; the action of the orthoformic ester gives tri(2-hydroxy-3,5-di-tert-butylphenyl)methane in a 90percent yield and under the Duff react
