64352-98-3Relevant articles and documents
Triazine-Based Cationic Leaving Group: Synergistic Driving Forces for Rapid Formation of Carbocation Species
Fujita, Hikaru,Kakuyama, Satoshi,Fukuyoshi, Shuichi,Hayakawa, Naoko,Oda, Akifumi,Kunishima, Munetaka
, p. 4568 - 4580 (2018/04/26)
A new triazine-based cationic leaving group has been developed for the acid-catalyzed alkylation of O- and C-nucleophiles. There are two synergistic driving forces, namely, stable C=O bond formation and charge-charge repulsive effects, involved in the rapid generation of the carbocation species in the presence of trifluoromethanesulfonic acid (~200 mol %). Considerable rate acceleration of benzylation, allylation, and p-nitrobenzylation was observed as compared to the reactions with less than 100 mol % of the acid catalyst. The triazine-based leaving group showed superior p-nitrobenzylation yield and stability in comparison to common leaving groups, trichloroacetimidate and bromide. A plausible reaction mechanism (the cationic leaving group pathway) was proposed on the basis of mechanistic and kinetic studies, NMR experiments, and calculations.
Specific reactivity of 2,4,6-tri-tert-butylanilide anions and its application to benzylation reagent
Yamada, Tomoyuki,Tsukagoshi, Shiori,Kitagawa, Osamu
supporting information, p. 317 - 320 (2017/01/03)
The reaction of methyl iodide with an anilide anion prepared from 2,4,6-tri-tert-butylanilide and NaH in CH3CN gave N-methyl anilide (N-alkylation product) as a major product, while in the reaction of benzyl bromide with the anilide anion in DMF, O-benzyl imidate (O-alkylation product) was obtained with almost complete selectivity. The treatment of O-benzyl imidate with alcohols and carboxylic acids in the presence of trifluoromethane sulfonic acid gave benzyl ethers and benzyl esters, respectively.
TRIAZINE DIONE COMPOUND
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Paragraph 0125-0127, (2017/07/11)
PROBLEM TO BE SOLVED: To provide a novel triazine dione compound useful as an alkylating agent for a nucleophilic compound. SOLUTION: This invention relates to a compound represented by formula (I) [where each symbol is as defined in the specification] and an alkylating agent comprising the compound, and a method for alkylating a nucleophilic compound using the alkylating agent. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT