51473-88-2Relevant academic research and scientific papers
Development of triazine-based benzylating reagents possessing T-butyl group on the triazine core: Thermally controllable reagents for the initiation of reaction
Karuo, Yukiko,Yamada, Kohei,Kunishima, Munetaka
, p. 303 - 308 (2018)
Benzylating reagents, 4-(4,6-di-t-butyl-1,3,5-triazin-2-yl)-4-benzylmorpholinium triflate, and related derivatives have been developed. The reagents release benzyl triflate as a benzyl cation equivalent upon heating the solution to 40°C under neutral conditions. The O-benzylation of alcohols using a stoichiometric amount of these reagents afforded corresponding benzyl ethers in good to high yields. This was due to the presence of a bulky t-butyl group on the triazine ring of these reagents that prevents the consumption of benzyl triflate via a side reaction with a morpholinotriazine derivative.
The aminolysis and hydrolysis of N-(4,6-diphenoxy-1,3,5-triazin-2-yl) substituted pyridinium salts: concerted displacement mechanism
Cullum, Neil R.,Rettura, Donatella,Whitmore, James M. J.,Williams, Andrew
, p. 1559 - 1564 (2007/10/03)
Reaction of the title pyridinium salts in aqueous buffers containing amines involves nucleophilic displacement of the pyridine by the amine nitrogen in addition to background hydrolysis.The second-order rate constants for attack of a series of unhindered primary amines on the (4,6-diphenoxy-1,3,5-triazin-2-yl)pyridinium cation obey a Broensted-like equation with slope βnuc = 0.68.Six-membered-ring cyclic secondary amines have a similar Broensted selectivity but are approximately 10-fold more reactive than primary amines of similar pKa.The reactivity of ethanolamine against the title pyridinium salts obeys a Broensted-like equation with βlg = -0.47.In aminolysis of the triazinyl pyridinium salts the changes in bomd fission and bond formation signalled by the polar substituent effects give Leffler α1g and αnuc values of 0.38 and 0.54, respectively, which indicate strong coupling between the bonding changes consistent with a concerted process for the displacement reaction.The adduct in the putative stepwise mechanism is considered too reactive to possess a significant barrier for it to exist as a discrete molecule.
