17348-59-3Relevant articles and documents
Kinetics and mechanism of N-Boc cleavage: Evidence of a second-order dependence upon acid concentration
Ashworth, Ian W.,Cox, Brian G.,Meyrick, Brian
, p. 8117 - 8125 (2010)
The kinetics of the HCl-catalyzed deprotection of the Boc-protected amine, thioester 2 to liberate AZD3409 1 have been studied in a mixture of toluene and propan-2-ol. The reaction rate was found to exhibit a second-order dependence upon the HCl concentration. This behavior was found to have a degree of generality as the deprotection of a second Boc-protected amine, tosylate 3 to yield amine 4 using HCl, sulfuric acid, and methane sulfonic acid showed the same kinetic dependence. In contrast the deprotection of tosylate 3 with trifluoroacetic acid required a large excess of acid to obtain a reasonable rate of reaction and showed an inverse kinetic dependence upon the trifluoroacetate concentration. These observations are rationalized mechanistically in terms of a general acid-catalyzed separation of a reversibly formed ion-molecule pair arising from the fragmentation of the protonated tert-butyl carbamate.
Kinetics of the reactions of tert-butanol with C2-C5 alcohols on sulfo cation exchangers
Golovanov,Pisareva,Levshenkov
, p. 179 - 183 (2013/05/22)
The kinetics of etherification of tert-butanol with aliphatic alcohols on gel KU-2×8 and macroporous KU-23 sulfo cation exchangers was studied. The first order of reaction with respect to tert-butanol and the -SO3H groups of a catalyst was established. The activation energy of the process observed on KU-2×8 was 60-95 kJ/mol. It was shown that the etherification of tert-butanol on KU-2×8 occurred in a surface layer. The reactivity of primary alcohols introduced into the reaction with tert-butanol increased with their molecular weights (C2-C5). The rate of reaction with secondary alcohols was lower than that with primary alcohols.
The first non-acid catalytic synthesis of tert-butyl ether from tert-butyl alcohol using ionic liquid as dehydrator
Shi, Feng,Xiong, Hai,Gu, Yanlong,Guo, Shu,Deng, Youquan
, p. 1054 - 1055 (2007/10/03)
Methyl tert-butyl ether (MTBE), ethyl tert-butyl ether (ETBE), and isopropyl tert-butyl ether (IPTBE) have been synthesized for the first time over a non-acid ionic liquid as catalyst and dehydrator with high conversion (> 90%) and selectivity (> 90%) under mild conditions.